US7727981B2 - Benzamides and related inhibitors of factor Xa - Google Patents
Benzamides and related inhibitors of factor Xa Download PDFInfo
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- US7727981B2 US7727981B2 US11/924,480 US92448007A US7727981B2 US 7727981 B2 US7727981 B2 US 7727981B2 US 92448007 A US92448007 A US 92448007A US 7727981 B2 US7727981 B2 US 7727981B2
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- phenyl
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Classifications
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/60—Salicylic acid; Derivatives thereof
- A61K31/612—Salicylic acid; Derivatives thereof having the hydroxy group in position 2 esterified, e.g. salicylsulfuric acid
- A61K31/616—Salicylic acid; Derivatives thereof having the hydroxy group in position 2 esterified, e.g. salicylsulfuric acid by carboxylic acids, e.g. acetylsalicylic acid
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/20—Pills, tablets, discs, rods
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/20—Pills, tablets, discs, rods
- A61K9/2004—Excipients; Inactive ingredients
- A61K9/2013—Organic compounds, e.g. phospholipids, fats
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/20—Pills, tablets, discs, rods
- A61K9/2004—Excipients; Inactive ingredients
- A61K9/2022—Organic macromolecular compounds
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Definitions
- R 1e is a member selected from the group of —F, —Cl, —Br, —OH, -Me and —OMe.
- the invention provides compound of formula Ib, as described above, having the following stricture:
- the invention provides a compound of formula Ib, as described above, having the following structure:
- each G group is substituted by 0-4 R 1d groups and each such R 1d group is independently selected from the group consisting of:
- amidino groups illustrated above as substituents for the cyclized amine heterocyclic ring are instead form an acyclic amidino A-Q group and all pharmaceutically acceptable isomers, salts, hydrates, solvates and prodrug derivatives thereof.
- Dosage formulations of the compounds of this invention to be used for therapeutic administration must be sterile. Sterility is readily accomplished by filtration through sterile membranes such as 0.2 micron membranes, or by other conventional methods. Formulations typically will be stored in lyophilized form or as an aqueous solution.
- the pH of the preparations of this invention typically will be 3-11, more preferably 5-9 and most preferably 7-8. It will be understood that use of certain of the foregoing excipients, carriers, or stabilizers will result in the formation of cyclic polypeptide salts.
- While the preferred route of administration is by injection, other methods of administration are also anticipated such as orally, intravenously (bolus and/or infusion), subcutaneously, intramuscularly, colonically, rectally, nasally, transdermally or intraperitoneally, employing a variety of dosage forms such as suppositories, implanted pellets or small cylinders, aerosols, oral dosage formulations and topical formulations such as ointments, drops and dermal patches.
- the compounds of this invention are desirably incorporated into shaped articles such as implants which may employ inert materials such as biodegradable polymers or synthetic silicones, for example, Silastic, silicone rubber or other polymers commercially available.
- Diagnostic applications of the compounds of this invention will typically utilize formulations such as solution or suspension.
- the compounds of this invention may be utilized in compositions such as tablets, capsules or elixirs for oral administration, suppositories, sterile solutions or suspensions or injectable administration, and the like, or incorporated into shaped articles.
- Subjects in need of treatment (typically mammalian) using the compounds of this invention can be administered dosages that will provide optimal efficacy.
- the dose and method of administration will vary from subject to subject and be dependent upon such factors as the type of mammal being treated, its sex, weight, diet, concurrent medication, overall clinical condition, the particular compounds employed, the specific use for which these compounds are employed, and other factors which those skilled in the medical arts will recognize.
- dissolution or suspension of the active compound in a vehicle such as an oil or a synthetic fatty vehicle like ethyl oleate, or into a liposome may be desired.
- a vehicle such as an oil or a synthetic fatty vehicle like ethyl oleate
- Buffers, preservatives, antioxidants and the like can be incorporated according to accepted pharmaceutical practice.
- Step 2 To a solution of 4-bromo-2-nitroaniline (43.4 mg, 0.2 mmol, 2.0 equiv) in 5 ml of methylene chloride treated with AlMe 3 (2M in hexane, 0.3 mL, 6 equiv) for 30 min was added methyl 2-(4-[(2-methylsulfonyl)phenyl]phenylcarbonyl)aminobenzoate (46.6 mg, 1 equiv). The mixture was stirred at rt overnight, quenched with saturated aqueous potassium sodium tartrate. The organic layer was dried over MgSO 4 , filtered and evaporated.
- Step 2 To A solution of 2-amino-5-bromopridine (135 mg, 4.0 equiv) in 5 mL of methylene chloride treated with AlMe 3 (2M in hexane, 1 mL, 10 equiv) for 30 min was added methyl 2-(4-[(2-t-butylaminosulfonyl)phenyl]phenylcarbonyl)amino-4-nitrobenzoate (100 mg, 0.2 mmol, 1 equiv). The mixture was stirred at rt overnight, quenched with saturated aqueous potassium sodium tartrate.
- Step 1 To a solution of 5-methyl-2-nitrobenzoic acid (1 g, 5.52 mmol) in dichloromethane (5 ml) was added oxalyl chloride (0.964 ml, 11.04 mmol) and a few drops of dimethylformamide. The mixture was stirred at r.t. for 2 hrs. After the evaporation of the solvent, the residue was dissolved in dichloromethane (5 ml). 2-amino-5-chloropyridine (852 mg, 6.62 mmol) and pyridine (1.34 ml, 16.56 mmol) were added to the solution. The mixture was stirred at r.t. overnight.
- Step 3 A mixture of N-(5-bromo-2-pyridinyl)-(2-(4-hydroxyamidinophenylcarbonyl)amino)5-fluorophenylcarboxamide (0.56 g, 1.19 mmol, 1.0 equiv) and zinc dust (0.39 g, 5.0 equiv), in 10 mL of acetic acid was stirred at rt for 45 min. The volatile was filtered and evaporated.
- Example 284 To a solution of Example 284 (10 mg) in MeOH (1 mL) was added 50 ⁇ L of 1N aq. LiOH solution. The mixture was stirred for 1 hour and purified by RP-HPLC to give the title compound. MS found for C 24 H 22 ClN 5 O 5 (M+H) + : 496.
- Step 1 A solution of methyl 2-amino-5-nitrobenzoate (1 equiv) and 4-cyanobenzoic acid (1 equiv) in pyridine was treated with POCl 3 (1.1 equiv) for 1 h. The resulting mixture was quenched by slow addition of water, and extracted with EtOAc. The organic layer was dried over MgSO 4 , filtered and flash chromatographied to give the desired product.
- Step 2 A solution of 2-amino-5-bromopridine (45 mg, 4.0 equiv) in 5 mL of methylene chloride treated with AlMe 3 (2M in hexane, 0.65 mL, 20 equiv) for 30 min was added the compound obtained in step 1 (0.064 mmol, 1 equiv). The mixture was stirred at rt overnight, quenched with saturated aqueous potassium sodium tartrate. The organic layer was dried over MgSO 4 , filtered, evaporated and purified by column chromatography to give the desired product.
- Step 3 The product obtained in step 2 was subjected to standard Pinner conditions to give the title compound after HPLC (C18 reversed phase, eluting with 0.5% TFA in H 2 O/CH 3 CN). MS (M+H) + : 467.
- Example 297 (1 equiv) in CH 2 Cl 2 was treated with BBr 3 (4 equiv) overnight, quenched with ice water. HPLC (C18 reversed phase, eluting with 0.5% TFA in H 2 O/CH 3 CN) gave the title compound. MS (M+H) + : 438.
- Step 1 A mixture of 4-cyanobenzaldehyde (1 equiv), 4-chloro-2-(5-chloro-2-pyridinyl)amino-carbonyl aniline (1 equiv) and glacial acetic acid (10 equiv) in CH 2 Cl 2 was stirred at rt for 30 min. NaBH(OAc) 3 (3 equiv) was added at once and the mixture was stirred overnight. The reaction was quenched with water and the organic layer was washed with brine and dried over Na 2 SO 4 . Column separation over silica gel gave the desired product.
- Step 2 A solution of the compound obtained in step 3 (1S mg) in anhydrous pyridine (10 mL) and triethyl amine (2 mL) was saturated with hydrogen sulfide gas at 0° C. The mixture was stirred at rt overnight. After concentration, the residue was dissolved in anhydrous acetone (10 mL) and iodomethane (1 mL) was added. The mixture was refluxed for 2 hrs. After concentration, the residue was dissolved in anhydrous methanol (5 mL) and a solution of pyrrolidine 0.5 mL) and acetic acid (0.5 mL) in anhydrous methanol (5 ml) was added. The mixture was refluxed for 15 min. After concentrated, the crude residue was purified by RP-HPLC to give target. MS (M+H) 435.
- Step 3 A solution of the compound obtained in step 2 (IS mg) in anhydrous pyridine (10 mL) and triethyl amine (2 mL) was saturated with hydrogen sulfide gas at 0° C. The mixture was stirred at rt overnight. After concentration, the residue was dissolved in anhydrous acetone (10 mL) and iodomethane (1 mL) was added. The mixture was refluxed for 2 hrs. After concentration, the residue was dissolved in anhydrous methanol (5 mL) and a solution of pyrrolidine (0.5 mL) and acetic acid (0.5 mL) in anhydrous methanol (5 ml) was added. The mixture was refluxed for 15 min. After concentrated, the crude residue was purified by RP-HPLC to give target. MS (M+H) 434.
Abstract
Description
A-Q-D-E-G-J-X (I)
where:
- A is selected from:
- (a) C1-C6-alkyl;
- (b) C3-C8-cycloalkyl;
- (c) —N(R1,R2), N(R1,R2)—C(═NR3)—, N(R1,R2)—C(═NR3)—N(R4)—, R1—C(═NR3)—, R1—C(═NR3)—N(R4)—;
- (d) phenyl, which is independently substituted with 0-2 R substitutents;
- (e) naphthyl, which is independently substituted with 0-2 R substituents;
and - (f) a monocyclic or fused bicyclic heterocyclic ring system having from 5 to 10 ring atoms, wherein 1-4 ring atoms of the ring system are selected from N, O and S, and wherein the ring system may be substituted with 0-2 R substituents;
- R is selected from:
- H, halo, —CN, —CO2R1, —C(═O)—N(R1, R2), —(CH2)m—CO2R1, —(CH2)m—C(═O)—N(R1, R2), —NO2, —SO2N(R1, R2), —SO2R1, —(CH2)m—NR1R2, —(CH2)m—C(═NR3)—R1, —(CH2)m—C(═NR3)—N(R1,R2), —(CH2)m—N(R4)—C(═NR3)—N(R1,R2), —(CH2)mNR1— group appended to a 3 to 6 membered heterocyclic ring containing from 1-4 heteroatoms selected from N, O and S, —C1-4alkyl, —C2-6alkenyl, —C2-6alkynyl, —C3-8cycloalkyl, —C0-4alkylC3-8cycloalkyl, —CF3, —OR2, and a 5-6 membered heterocyclic system containing from 1-4 heteroatoms selected from N, O and S, wherein from 1-4 hydrogen atoms on the heterocyclic system may be independently replaced with a member selected from the group consisting of halo, —C1-C4-alkyl, —C1-4alkyl-CN, —C2-6alkenyl, —C2-6alkynyl, —C3-8cycloalkyl, —C0-4alkylC3-8cycloalkyl and —NO2;
- m is an integer of 0-2;
- R1, R2, R3 and R4 are independently selected from the group consisting of:
- H, —OR5, —N(—R5, —R6), —C1-4alkyl, —C2-6alkenyl, —C2-6alkynyl, —C3-8cycloalkyl, —C0-4alkylC3-8cycloalkyl, —C0-4alkylphenyl and —C0-4alkylnaphthyl, wherein from 1-4 hydrogen atoms on the ring atoms of the phenyl and naphthyl moieties may be independently replaced with a member selected from the group consisting of halo, —C1-4alkyl, —C2-6alkenyl, —C2-6alkynyl, —C3-8cycloalkyl, —C0-4alkylC3-8cycloalkyl, —CN, and —NO2; or
- R1 and R2, or R2 and R3 taken together can form a 3-8 membered cycloalkyl or a heterocyclic ring system, wherein the heterocyclic ring system may have from 3 to 10 ring atoms, with 1 to 2 rings being in the ring system and contain from 1-4 heteroatoms selected from N, O and S, wherein from 1-4 hydrogen atoms on the heterocyclic ring system may be independently replaced with a member selected from the group consisting of halo, C1-C4-alkyl, —CN—C1-4alkyl, —C2-6alkenyl, —C2-6alkynyl, —C3-8cycloalkyl, —C0-4alkylC3-8cycloalkyl and —NO2;
- R5 and R6 are independently selected from the group consisting of:
- H, —C1-4alkyl, —C2-6alkenyl, —C2-6alkynyl, —C3-8cycloalkyl, —C0-4alkylC3-8cycloalkyl, —C0-4alkylphenyl and —C0-4alkylnaphthyl, wherein from 1-4 hydrogen atoms on the ring atoms of the phenyl and naphthyl moieties may be independently replaced with a member selected from the group consisting of halo, —C1-4alkyl, —C2-6alkenyl, —C2-6alkynyl, —C3-8cycloalkyl, —C0-4alkylC3-8cycloalkyl, —CN, and —NO2; or
- R5 and R6 taken together can form a 3-8 membered cycloalkyl or a heterocyclic ring system, wherein the heterocyclic ring system may have from 3 to 10 ring atoms, with 1 to 2 rings being in the ring system and contain from 1-4 heteroatoms selected from N, O and S, wherein from 1-4 hydrogen atoms on the heterocyclic ring system may be independently replaced with a member selected from the group consisting of halo, —C1-C4-alkyl, —CN—C1-4alkyl, —C2-6alkenyl, —C2-6alkynyl, —C3-8cycloalkyl, —C0-4alkylC3-8cycloalkyl and —NO2;
- Q is a member selected from the group consisting of:
- a direct link, —CH2—, —C(═O)—, —O—, —N(R7)—, —N(R7)CH2—, —CH2N(R7)—, —C(═NR7)—, —C(═O)—N(R7)—, —N(R7)—C(═O)—, —S—, —SO—, —SO2—, —SO2—N(R7)— and —N(R7)—SO2—;
- R7 is selected from:
- H, —C1-4alkyl, —C2-6alkenyl, —C2-6alkynyl, —C3-8cycloalkyl, —C0-4alkylC3-8cycloalkyl, —C0-4alkylphenyl and —C0-4alkylnaphthyl, wherein from 1-4 hydrogen atoms on the ring atoms of the phenyl and naphthyl moieties may be independently replaced with a member selected from the group consisting of halo, —C1-4alkyl, —C2-6alkenyl, —C2-6alkynyl, —C3-8cycloalkyl, —C0-4alkylC3-8cycloalkyl, —CN, and —NO2;
- D is a direct link or is a member selected from the group consisting of:
- (a) phenyl, which is independently substituted with 0-2 R1a substituents;
- (b) naphthyl, which is independently substituted with 0-2 R1a substituents; and
- (c) a monocyclic or fused bicyclic heterocyclic ring system having from 5 to 10 ring atoms, wherein 1-4 ring atoms of the ring system are selected from N, O and S, and wherein the ring system may be substituted from 0-2 R1a substituents;
- R1a is selected from:
- halo, —C1-4alkyl, —C2-6alkenyl, —C2-6alkynyl, —C3-8cycloalkyl, —C0-4alkylC3-8cycloalkyl, —CN, —NO2, —(CH2)nNR2aR3a, —(CH2)nCO2R2a, —(CH2)nCONR2aR3a, —SO2NR2aR3a, —SO2R2a, —CF3, —OR2a, and a 5-6 membered aromatic heterocyclic system containing from 1-4 heteroatoms selected from N, O and S, wherein from 1-4 hydrogen atoms on the aromatic heterocyclic system may be independently replaced with a member selected from the group consisting of halo, —C1-4alkyl, —C2-6alkenyl, —C2-6alkynyl, —C3-8cycloalkyl, —C0-4alkylC3-8cycloalkyl, —CN and —NO2,
- R2a and R3a are independently selected from the group consisting of:
- H, —C1-4alkyl, —C2-6alkenyl, —C2-6alkynyl, —C3-8cycloalkyl, —C0-4alkylC3-8cycloalkyl, —C0-4alkylphenyl and —C0-4alkylnaphthyl, wherein from 1-4 hydrogen atoms on the ring atoms of the phenyl and naphthyl moieties may be independently replaced with a member selected from the group consisting of halo, —C1-4alkyl, —C2-6alkenyl, —C2-6alkynyl, —C3-8cycloalkyl, —C0-4alkylC3-8cycloalkyl, —CN and —NO2;
- n is an integer of 0-2;
- E is a direct link or a member selected from the group consisting of:
- —C1-2-alkyl-, —O—, —S—, —SO—, —SO2—, —C0-1-alkyl-C(═O), —C0-1-alkyl-C(═O)—N(—R8)—C0-1-alkyl-, —C0-1-alkyl-N(—R8)—C(═O)—C0-1-alkyl-, —N(—R8)—C(═O)—N(—R8)— and —C0-1-alkyl-N(—R8)—;
- R8 is a member selected from the group consisting of:
- H; —C1-4-alkyl; —C0-4-alkylaryl; —C0-4-alkyl-heteroaryl; —C1-4-alkyl-C(═O)—OH, —C1-4-alkyl-C(═O)—O—C1-4-alkyl, and —C1-4-alkyl-C(═O)—N(—R2b, —R3b);
- R2b and R3b are each a member independently selected from the group consisting of:
- H, —C1-4-alkyl, —C0-4-alkyl-aryl; —C0-4-alkyl-heterocyclic group, and R2b and R3b together with the N atom to which they are attached can form a 5-8 membered heterocyclic ring containing 1-4 heteroatoms selected from N, O and S, wherein the heterocyclic ring may be substituted with 0-2 R1c groups;
- R1c is a member selected from the group consisting of:
- Halo; —C1-4-alkyl; —CN, —NO2; —C(═O)—N(—R2c, —R3c); —C(═O)—OR2c; —(CH2)q—N(—R2c, —R3c); —SO2—N(—R2c, —R3c); —SO2R2c; —CF3 and —(CH2)q—OR2c;
- R2c and R3c are each independently a member selected from the group consisting of:
- H; —C1-4-alkyl and —C1-4-alkyl-aryl;
- q is an integer of 0-2;
- G is a member selected from the group consisting of:
- (a) C2-alkenyl or C3-8-cycloalkenyl, wherein the alkenyl and cycloalkenyl attachment points are the alkenyl carbon atoms and wherein the —C2-alkenyl or —C3-8-cycloalkenyl are substituted with 0-4 R1d groups;
- (b) a phenylene group wherein the ring carbon atoms of the phenylene group are substituted with 0-4 R1d groups;
- (c) a 3-8 membered a saturated, partially unsaturated or aromatic monocyclic-heterocyclic ring system containing 1-4 heteroatoms selected from N, O and S, wherein 0-2 ring atoms of the heterocyclic ring may be substituted with 0-4 R1d groups; and,
- (d) an 8-10 membered fused heterocyclic bicyclic ring system, containing 1-4 heteroatoms selected from N, O and S, wherein 0-2 ring atoms of the fused bicyclic ring system may be substituted with 0-4 R1d groups;
- R1d is a member selected from the group consisting of:
- H, halo; C1-6-alkyl, carbocylic aryl, —CN; —NO2; —(CH2)0-6—NR2dR3d; —SO2NR2dR3d; —SO2R2d; —CF3; —(CH2)0-6—OR2d; —OH, —OC1-6alkyl, —O—(CH2)1-6OR2d; —O—(CH2)1-6—C(═O)—O—R2d; —O—(CH2)1-6—C(═O)—N(R2d,R3d); —N(R5a)—(CH2)1-6—OR2d; —N(R5a)—(CH2)1-6—N(R2d,R3d); —C(═O)—N(R2d,R3d); —N(R5a)—(CH2)1-6—C(═O)—N(R2d,R3d); —N(—(CH2)1-6—OR2d)2; —N(R5a)—(CH2)1-6—OR2d; —N(R5a)—C(═O)—R2d; —N(R5a)—SO2—R2d; —(CH2)0-6—C(═O)—O—R2d; —(CH2)0-6—C(═O)—N(R2d,R3d); —(CH2)0-6—C(═NR2d)—O—R2d; —(CH2)0-6—N(R5a)C(═NR2d)—N(R3d,R4d); a —(CH2)0-6—N(R3d)C5-6 membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1-4 heteroatoms selected from N, O and S, and a —(CH2)0-6-5-6 membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1-4 heteroatoms selected from N, O and S;
- R5a, R2d, R3d and R4d are each independently a member selected from the group consisting of:
- H, C1-6-alkyl and C1-6-alkylaryl, —CN; —NO2; carbocylic aryl, —CN; —NO2; or
- R2d and R3d taken together with the N atoms they are independently attached form a 5-7 membered saturated, partially unsaturated or aromatic heterocyclic ring; or
- R3d and R4d taken together with the N atom to which they are attached form a 5-8 membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1-4 heteroatoms selected from N, O and S;
- J is a direct link or is a member selected from the group consisting of:
- —N(—R9)—C(═O)—; —C(═O)—N(—R9)—; —O—; —S—; —SO—; —SO2—; —CH2—; —N(—R9)—; and —N(—R9)—SO2—;
- R9 is a member selected from the group consisting of:
- H; —C1-4-alkyl; —C0-4-alkyl-carbocyclic aryl; —(CH2)0-4-5-6 membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1-4 heteroatoms selected from N, O and S; —(CH2)1-6—C(═O)—O—C1-4-alkyl; and —(CH2)1-6—C(═O)—N(R6a,R6b);
- R6a and R6b are each a member independently selected from the group consisting of:
- H and —C1-6-alkyl;
- X is a member selected from the group consisting of:
- (a) phenyl substituted with 0-3 R1e groups;
- (b) naphthyl substituted with 0-3 R1e groups and
- (c) a 6-membered aromatic heterocyclic ring system containing 1-3 N atoms and having 0-3 ring atoms substituted with 0-3 R1e groups; and
- (d) an 8-10 membered fused aromatic heterocyclic bicyclic ring system containing 1-4 heteroatoms selected from N, O and S and 0-3 ring atoms of the fused heterocyclic bicyclic ring system are substituted with 0-3 R1e groups;
- R1e is a member independently selected from the group consisting of:
- Halo; CF3; —C1-4-alkyl; carbocyclic aryl; —C0-2-alkyl-CN; —O—R2e; —C0-2-alkyl-C(═O)—O—R2e; —C0-2-alkyl-C(═O)—N(R2e, R3e); —C0-2-alkyl-NO2; —C0-2-alkyl-N(R2e, R3e); —C0-2-alkyl-SO2—N(R2e, R3e); —C0-2-alkyl-SO2—R2e; trihaloalkyl; —O—C0-2alkyl-O—R2e; —C0-2-alkyl-O—R2e; —O—C1-4-alkyl-C(═O)—N(R2e, R3e); —O—C1-4-alkyl-C(═O)—O—R2e; —C0-2-alkyl-N(R2e)—C(═O)—R3e; —C0-2-alkyl-N(—R2e)—SO2—R3e; —CH2—N(R2e)—C(═O)—R3e; —CH2—N(R2e)—SO2—R3e; —(CH2)0-6NR2eR3e; —C(═O)—N(R2e,R3e); —N(—(CH2)1-6—OR2e)2; —N(R10)—(CH2)1-6—OR2e; —N(R10)—C(═O)—R2e; —N(R10)—SO2—R2e; —C(═N(R10))—N(R2e,R3e); and a —(CH2)0-6-5-6 membered saturated, partially unsaturated or aromatic heterocyclic ring containing 14 heteroatoms selected from N, O and S;
- R10, R2e and R3w are each independently a member selected from the group consisting of:
- H; —C1-4-alkyl; —C0-2-alkyl-O—R1g; —C0-2-alkyl-N(—R1g, —R2g); —C1-4-alkyl-carbocyclic aryl; —C1-4-alkyl-heterocyclic; and R10 and R2e, or R2e and R3e together with the N atom to which they are attached can form 5-8 membered heterocyclic ring containing 1-4 heteroatoms selected from N, O and S which can be substituted with 0-2 R1g groups;
- R1g and R2g are independently a member selected from the group of:
- H; halo; —C1-4-alkyl, a carbocyclic aryl group; a saturated, partially unsaturated or aromatic heterocyclic group; —CN; —C(═O)—N(R3g)R4g; —C(═O)—OR3g; —NO2; —(CH2)p—NR3gR4g; —SO2NR3gR4g; —SO2R3g; —CF3; and —(CH2)pOR3g;
- p is an integer of 0-2;
- R3g and R4g are each independently selected from the group consisting of:
- H; C1-4-alkyl and —C0-4-alkyl-carbocyclic aryl;
- and all pharmaceutically acceptable isomers, salts, hydrates, solvates and prodrug derivatives thereof.
A-Q-D-E-G-J-X (I)
where:
- A is selected from:
- (a) C1-C6-alkyl;
- (b) C3-C8-cycloalkyl;
- (c) —N(R1,R2), N(R1,R2)—C(═NR3)—, N(R1,R2)—C(═NR3)—N(R4), R1—C(═NR3)—, R1—C(═NR3)—N(R4)—;
- (d) phenyl, which is independently substituted with 0-2 R substituents;
- (e) naphthyl, which is independently substituted with 0-2 R substituents;
and - (f) a monocyclic or fused bicyclic heterocyclic ring system having from 5 to 10 ring atoms, wherein 1-4 ring atoms of the ring system are selected from N, O and S, and wherein the ring system may be substituted with 0-2 R substituents;
- R is selected from:
- H, halo, —CN, —CO2R1, —C(═O)—N(R1, R2), —(CH2)m—CO2R1, —(CH2)m—C(═O)—N(R1, R2), —NO2, —SO2N(R1, R2), —SO2R1, —(CH2)mNR1R2; —(CH2)m—C(═NR3)—R1, —(CH2)m—C(═NR3)—N(R1,R2), (CH2)m—N(R4)—C(═NR3)—N(R1,R2), —(CH2)mNR1—C3-6heterocyclics, C1-4alkyl, C2-6alkenyl, C2-6alkynyl, C3-8cycloalkyl, C0-4alkylC3-8cycloalkyl, —CF3, —OR2, and a 5-6 membered heterocyclic system containing from 1-4 heteroatoms selected from N, O and S, wherein from 1-4 hydrogen atoms on the heterocyclic system may be independently replaced with a member selected from the group consisting of halo, C1-C4-alkyl, CN—C1-4alkyl, —C2-6alkenyl, —C2-6alkynyl, —C3-8cycloalkyl, —C0-4alkylC3-8cycloalkyl and —NO2;
- m is an integer of 0-2;
- R1, R2, R3 and R4 are independently selected from the group consisting of:
- H, —OR5, —N(—R5, —R6), —C1-4alkyl, —C2-6alkenyl, —C2-6alkynyl, —C3-8cycloalkyl, —C0-4alkylC3-8cycloalkyl, —C0-4alkylphenyl and —C0-4alkylnaphthyl, wherein from 1-4 hydrogen atoms on the ring atoms of the phenyl and naphthyl moieties may be independently replaced with a member selected from the group consisting of halo, —C1-4alkyl, —C2-6alkenyl, —C2-6alkynyl, —C3-8cycloalkyl, —C0-4alkylC3-8cycloalkyl, —CN, and —NO2; or
- R1 and R2, or R2 and R3 taken together can form a 3-8 membered cycloalkyl or a heterocyclic ring system, wherein the heterocyclic ring system may have from 3 to 10 ring atoms, with 1 to 2 rings being in the ring system and contain from 1-4 heteroatoms selected from N, O and S, wherein from 1-4 hydrogen atoms on the heterocyclic ring system may be independently replaced with a member selected from the group consisting of halo, C1-C4-alkyl, —CN—C1-4alkyl, —C2-6alkenyl, —C2-6alkynyl, —C3-8cycloalkyl, —C0-4alkylC3-8cycloalkyl and —NO2;
- R5 and R6 are independently selected from the group consisting of:
- H, —C1-4alkyl, —C2-6alkenyl, —C2-6alkynyl, —C3-8cycloalkyl, —C0-4alkylC3-8cycloalkyl, —C0-4alkylphenyl and —C0-4alkylnaphthyl, wherein from 1-4 hydrogen atoms on the ring atoms of the phenyl and naphthyl moieties may be independently replaced with a member selected from the group consisting of halo, —C1-4alkyl, —C2-6alkenyl, —C2-6alkynyl, —C3-8cycloalkyl, —C0-4alkylC3-8cycloalkyl, —CN, and —NO2; or
- R5 and R6 taken together can form a 3-8 membered cycloalkyl or a heterocyclic ring system, wherein the heterocyclic ring system may have from 3 to 10 ring atoms, with 1 to 2 rings being in the ring system and contain from 1-4 heteroatoms selected from N, O and S, wherein from 1-4 hydrogen atoms on the heterocyclic ring system may be independently replaced with a member selected from the group consisting of halo, C1-C4-alkyl, —CN—C1-4alkyl, —C2-6alkenyl, —C2-6alkynyl, —C3-8cycloalkyl, —C0-4alkylC3-8cycloalkyl and —NO2;
- Q is a member selected from the group consisting of:
- a direct link, —CH2—, —C(═O)—, —O—, —N(R7)—, —N(R7)CH2—, —CH2N(R7)—, —C(═NR7)—, —C(═O)—N(R7)—, —N(R7)—C(═O)—, —S—, —SO—, —SO2—, —SO2—N(R7)— and —N(R7)—SO2—;
- R7 is selected from:
- H, —C1-4alkyl, —C2-6alkenyl, —C2-6alkynyl, —C3-8cycloalkyl, —C0-4alkylC3-8cycloalkyl, —C0-4alkylphenyl and —C0-4alkylnaphthyl, wherein from 1-4 hydrogen atoms on the ring atoms of the phenyl and naphthyl moieties may be independently replaced with a member selected from the group consisting of halo, —C1-4alkyl, —C2-6alkenyl, —C2-6alkynyl, —C3-8cycloalkyl, —C0-4alkylC3-8cycloalkyl, —CN, and —NO2;
- D is a direct link or is a member selected from the group consisting of:
- (a) phenyl, which is independently substituted with 0-2 R1a substituents;
- (b) naphthyl, which is independently substituted with 0-2 R12 substituents; and
- (c) a monocyclic or fused bicyclic heterocyclic ring system having from 5 to 10 ring atoms, wherein 1-4 ring atoms of the ring system are selected from N, O and S, and wherein the ring system may be substituted from 0-2 R1a substituents;
- R1a is selected from:
- halo, —C1-4alkyl, —C2-6alkenyl, —C2-6alkynyl, —C3-8cycloalkyl, —C0-4alkylC3-8cycloalkyl, —CN, —NO2, —(CH2)nNR2aR3a, —(CH2)nCO2R2a, —(CH2)CONR2aR3a, —SO2NR2aR3a, —SO2R2a, —CF3, —OR2a, and a 5-6 membered aromatic heterocyclic system containing from 1-4 heteroatoms selected from N, O and S, wherein from 1-4 hydrogen atoms on the aromatic heterocyclic system may be independently replaced with a member selected from the group consisting of halo, —C1-4alkyl, —C2-6alkenyl, —C2-6alkynyl, —C3-8cycloalkyl, —C0-4alkylC3-8cycloalkyl, —CN and —NO2;
- R2a and R3a are independently selected from the group consisting of:
- H, —C1-4alkyl, —C2-6alkenyl, —C2-6alkynyl, —C3-8cycloalkyl, —C0-4alkylC3-8cycloalkyl, —C0-4alkylphenyl and —C0-4alkylnaphthyl, wherein from 1-4 hydrogen atoms on the ring atoms of the phenyl and naphthyl moieties may be independently replaced with a member selected from the group consisting of halo, —C1-4alkyl, —C2-6alkenyl, —C2-6alkynyl, —C3-8cycloalkyl, —C0-4alkylC3-8cycloalkyl, —CN and —NO2;
- n is an integer of 0-2;
- E is a direct link or a member selected from the group consisting of:
- —C1-2-alkyl-, —O—, —S—, —SO—, —SO2—, —CO0-1-alkyl-C(═O)—, —C0-1-alkyl-C(═O)—N(—R8)—C0-1-alkyl-, —C0-1-alkyl-N(—R8)—C(═O)—C0-1-alkyl-, —N(—R8)—C(═O)—N(—R8)— and —C0-1-alkyl-N(—R8)—;
- R8 is a member selected from the group consisting of:
- H; —C1-4-alkyl; —C0-4-alkylaryl; —C0-4-alkyl-heteroaryl; —C1-4-alkyl-C(═O)—OH, —C1-4-alkyl-C(═O)—O—C1-4-alkyl, and —C1-4-alkyl-C(═O)—N(—R2b, —R3b);
- R2b and R3b are each a member independently selected from the group consisting of:
- H, —C1-4-alkyl, —C0-4-alkyl-aryl; —C0-4-alkyl-heterocyclic group, and R2b and R3b together with the N atom to which they are attached can form a 5-8 membered heterocyclic ring containing 1-4 heteroatoms selected from N, O and S, wherein the heterocyclic ring may be substituted with 0-2 R1c groups;
- R1c is a member selected from the group consisting of:
- Halo; —C1-4-alkyl; —CN, —NO2; —C(═O)—N(—R2c, —R3c); —C(═O)OR2c; —(CH2)q—N(—R2c, —R3c); —SO2—N(—R2c, —R3c); —SO2R2c; —CF3 and —(CH2)q—OR2c;
- R2c and R3c are each independently a member selected from the group consisting of:
- H; —C1-4-alkyl and —C1-4-alkyl-aryl;
- q is an integer of 0-2;
- G is a member selected from the group consisting of:
- (a) C2-alkenyl or C3-8-cycloalkenyl, wherein the alkenyl and cycloalkenyl attachment points are the alkenyl carbon atoms and wherein C2-alkenyl or C3-8-cycloalkenyl are substituted with 0-4 R1d groups;
- (b) a phenylene group wherein the ring carbon atoms of the phenylene group are substituted with 0-4 R1d groups;
- (c) a 3-8 membered a saturated, partially unsaturated or aromatic monocyclic-heterocyclic ring system containing 1-4 heteroatoms selected from N, O and S, wherein 0-4 ring atoms of the heterocyclic ring may be substituted with 0-4 R1d groups; and,
- (d) an 8-10 membered fused heterocyclic bicyclic ring system, containing 1-4 heteroatoms selected from N, O and S, wherein 0-4 ring atoms of the fused bicyclic ring system may be substituted with 0-4 R1d groups;
- R1d is a member selected from the group consisting of:
- H, halo; C1-6alkyl, carbocylic aryl, —CN; —NO2; —(CH2)0-6—NR2dR3d; —SO2 NR2dR3d; —SO2R2d; —CF3; —(CH2)0-6—OR2d; —OH, —OC1-6alkyl, —O—(CH2)1-6OR2d; —O—(CH2)1-6—C(═O)—O—R2d; —O—(CH2)1-6—C(═O)—N(R2dR3d); —N(R5a)—(CH2)1-6—OR2d; —N(R5a)—(CH2)1-6—N(R2d,R3d); —C(═O)—N(R2d,R3d); —N(R5a)—(CH2)1-6—C(═O)—N(R2dR3d); —N(—(CH2)1-6—OR2d)2; —N(R5a)—(CH2)1-6OR2d; —N(R5a)—C(═O)—R2d; —N(R5a)—SO2—R2d; —(CH2)0-6—C(═O)—O—R2d; —(C2)0-6—C(═O)—N(R2d,R3d); —(CH2)0-6—C(═NR2d)—N(R3d,R4d); —(CH2)0-6—N(R5a)C(═NR2d)—N(R3d,R4d); and —(CH2)0-6—N(—R3d)— group attached directly by its nitrogen atom to a carbon atom of a 5 to 6 membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1-4 heteroatoms selected from N, O and S, and a —(CH2)0-6— group attached to a 5-6 membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1-4 heteroatoms selected from N, O and S;
- R5a, R2d, R3d and R4d are each independently a member selected from the group consisting of:
- H, C1-6-alkyl and C1-6-alkylaryl, —CN; —NO2; carbocylic aryl, —CN; —NO2; or
- R2d and R3d taken together with the N atoms there are independently attached form a 5-7 membered saturated, partially unsaturated or aromatic heterocyclic ring; or
- R3d and R4d taken together with the N atom to which they are attached form a 5-8 membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1-4 heteroatoms selected from N, O and S;
- J is a direct link or is a member selected from the group consisting of:
- —N(—R9)—C(═O)—; —C(═O)—N(—R9)—; —O—; —S—; —SO—; —SO2—; —CH2—; —N(—R9)—; and —N(—R9)—SO2—;
- R9 is a member selected from the group consisting of:
- H; —C1-4-alkyl; —C0-4-alkyl-carbocyclic aryl; —(CH2)0-4-5-6 membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1-4 heteroatoms selected from N, O and S; —(CH2)1-6—C(═O)—O—C1-4-alkyl; and —(CH2)1-6—C(═O)—N(R6a,R6b);
- R6a and R6b are each a member independently selected from the group consisting of:
- H and —C1-6alkyl;
- X is a member selected from the group consisting of:
- (a) phenyl substituted with 0-3 R1e groups;
- (b) naphthyl substituted with 0-3 R1e groups;
- (c) a 6-membered aromatic heterocyclic ring system containing 1-3 N atoms and having 0-3 ring atoms substituted with 0-3 R1e groups; and
- (d) an 8-10 membered fused aromatic heterocyclic bicyclic ring system containing 1-4 heteroatoms selected from N, O and S and 0-3 ring atoms of the fused heterocyclic bicyclic ring system are substituted with 0-3 R1e groups;
- R1e is a member independently selected from the group consisting of:
- Halo; CF3; —C1-4-alkyl; carbocyclic aryl; —C0-2-alkyl-CN; —O—R2e; —C0-2-alkyl-C(═O)—O—R2e; —C0-2-alkyl-C(═O)—N(R2e, R3e); —C0-2-alkyl-NO2; —C0-2-alkyl-N(R2e, R3e); —C0-2-alkyl-SO2—N(R2e, R3e); —C0-2-alkyl-SO2—R2e; trihaloalkyl; —O—C0-2-alkyl-O—R2e; —C0-2-alkyl-O—R2e; —O—C1-4-alkyl-C(═O)—N(R2e, R3e); —O—C1-4-alkyl-C(═O)—O—R2e; —C0-2-alkyl-N(R2e)—C(═O)—R3e; —C0-2-alkyl-N(—R2e)—SO2—R3e; —CH2—N(R2e)—C(═O)—R3e; —CH2—N(R2e)—SO2—R3e; —(CH2)0-6NR2eR3e; —C(═O)—N(R2e,R3e); —N(—(CH2)1-6—OR2e)2; —N(R10)—(CH2)1-6—OR2e; —N(R10)—C(═O)—R2e; —N(R10)—SO2—R2e; —C(═N(R10))—N(R2e,R3e); and a —(CH2)0-6-5-6 membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1-4 heteroatoms selected from N, O and S;
- R10, R2e and R3e are each independently a member selected from the group consisting of:
- H; —C1-4alkyl; —C0-2-alkyl-O—R1g; —C0-2-alkyl-N(—R1g, —R2g); —C1-4-alkyl-carbocyclic aryl; —C1-4-alkyl-heterocyclic; and R10 and R2e, or R2e and R3e together with the N atom to which they are attached can form 5-8 membered heterocyclic ring containing 1-4 heteroatoms selected from N, O and S which can be substituted with 0-2 R1g groups;
- R1g and R2g are independently a member selected from the group of:
- H; halo; —C1-4-alkyl, a carbocyclic aryl group; a saturated, partially unsaturated or aromatic heterocyclic group; —CN; —C(═O)—N(R3g)R4g; —C(═O)—OR3g; —NO2; —(CH2)p—NR3gR4g; —SO2NR3gR4g; —SO2R3g; —CF3; and —(CH2)pOR3g;
- p is an integer of 0-2; and
- R3g and R4g are each independently selected from the group consisting of:
- H; C1-4-alkyl and —C0-4-alkyl-carbocyclic aryl;
A-Q-D-E-G-J-X (Ia)
where:
- A is selected from:
- (a) C1-C6-alkyl;
- (b) C3-C8-cycloalkyl;
- (c) —N(R1,R2), N(R1,R2)—C(═NR3)—, N(R1,R2)—C(═NR3)—N(R4)—, R1—C(═NR3)—, R1—C(═NR3)—N(R4)—;
- (d) phenyl, which is independently substituted with 0-2 R substituents;
- (e) naphthyl, which is independently substituted with 0-2 R substituents;
and - (f) monocyclic or fused bicyclic heterocyclic ring system having from 5 to 10 ring atoms, wherein 1-4 ring atoms of the ring system are selected from N, O and S, and wherein the ring system may be substituted with 0-2 R substituents;
- R is selected from:
- H, halo, —CN, —CO2R1, —C(═O)—N(R1, R2), —(CH2)m—CO2R1, —(CH2)m—C(═O)—N(R1, R2), —NO2, —SO2N(R1, R2), —SO2R1, —(CH2)mNR1R2, —(CH2)m—C(═NR3)—R1; —(CH2)m—C(═NR3)—N(R1,R2), —(CH2)m—N(R4)—C(═NR3)—N(R1,R2), (CH2)mNR1— group attached to a 3-6 membered heterocylic ring having from 1 to 3 heteroatoms selected from the group consisting of N, O and S, —C1-4alkyl, —C2-6alkenyl, —C2-6alkynyl, —C3-8cycloalkyl, —C0-4alkylC3-8cycloalkyl, —CF3, —OR2, and a 5-6 membered heterocyclic aromatic or partially saturated system, including imidazoline, containing from 1-4 heteroatoms selected from N, O and S, wherein from 1-4 hydrogen atoms on the heterocyclic system may be independently replaced with a member selected from the group consisting of halo, -methyl, —C2-C4-alkyl, —CN, —C2-6alkenyl, —C2-6alkynyl, —C3-8cycloalkyl, —C0-4alkylC3-8cycloalkyl and —NO2;
- m is an integer of 0-2;
- R1, R2, R3 and R4 are independently selected from the group consisting of:
- H, —OR5, —N(—R5, —R6), —C1-4alkyl, —C2-6alkenyl, —C2-6alkynyl, —C3-8cycloalkyl, —C0-4alkylC3-8cycloalkyl, —C0-4alkylphenyl and —C0-4alkylnaphthyl, wherein from 1-4 hydrogen atoms on the ring atoms of the phenyl and naphthyl moieties may be independently replaced with a member selected from the group consisting of halo, —C1-4alkyl, —C2-6alkenyl, —C2-6alkynyl, —C3-8cycloalkyl, —C0-4alkylC3-8cycloalkyl, —CN, and —NO2; or
- R1 and R2, or R2 and R3 taken together can form a 3-8 membered cycloalkyl or a heterocyclic ring system, wherein the heterocyclic ring system may have from 3 to 10 ring atoms, with 1 to 2 rings being in the ring system and contain from 1-4 heteroatoms selected from N, O and S, wherein from 1-4 hydrogen atoms on the heterocyclic ring system may be independently replaced with a member selected from the group consisting of halo, C1-C4-alkyl, —CN—C1-4alkyl, —C2-6alkenyl, —C2-6alkynyl, —C3-8cycloalkyl, —C0-4alkylC3-8cycloalkyl and —NO2;
- R5 and R6 are independently selected from the group consisting of:
- H, —C1-4alkyl, —C2-6alkenyl, —C2-6alkynyl, —C3-8cycloalkyl, —C0-4alkylC3-8cycloalkyl, —C0-4alkylphenyl and —C0-4alkylnaphthyl, wherein from 1-4 hydrogen atoms on the ring atoms of the phenyl and naphthyl moieties may be independently replaced with a member selected from the group consisting of halo, —C1-14alkyl, —C2-6alkenyl, —C2-6alkynyl, —C3-8cycloalkyl, —C0-4alkylC3-8cycloalkyl, —CN, and —NO2; or
- R5 and R6 taken together can form a 3-8 membered cycloalkyl or a heterocyclic ring system, wherein the heterocyclic ring system may have from 3 to 10 ring atoms, with 1 to 2 rings being in the ring system and contain from 1-4 heteroatoms selected from N, O and S, wherein from 1-4 hydrogen atoms on the heterocyclic ring system may be independently replaced with a member selected from the group consisting of halo, C1-C4-alkyl, —CN—C1-4alkyl, —C2-6alkenyl, —C2-6alkynyl, —C3-8cycloalkyl, —C0-4alkylC3-8cycloalkyl and —NO2;
- Q is a member selected from the group consisting of:
- a direct link, —CH2—, —C(═O)—, —O—, —NH—, —NMe-, —NHCH2—, —NMeCH2—, —CH2NH—, —C(═NH)—, —C(═O)—NH—, —NH—C(═O)—, —CH2NMe-, —C(—NMe)-;
- D is a direct link or is a member selected from the group consisting of:
-
- a monocyclic or fused bicyclic heterocyclic ring system having from 5 to 10 ring atoms, wherein 1-4 ring atoms of the ring system are selected from N, O and S, and wherein the ring system may be substituted from 0-2 R1a substituents;
- R1a is selected from:
- halo, —C1-4alkyl, —C2-6alkenyl, —C2-6alkynyl, —C3-8cycloalkyl, —C0-4alkylC3-8cycloalkyl, —CN, —NO2, —(CH2)nNR2aR3a, —(CH2)nCO2R2a, (CH2)nCONR2aR3a, —SO2NR2aR3a, —SO2R2a, —CF3, —OR2a, and a 5-6 membered aromatic heterocyclic system containing from 1-4 heteroatoms selected from N, O and S, wherein from 1-4 hydrogen atoms on the aromatic heterocyclic system may be independently replaced with a member selected from the group consisting of halo, —C1-4alkyl, —C2-6alkenyl, —C2-6alkynyl, —C3-8cycloalkyl, —C0-4alkylC3-8cycloalkyl, —CN and —NO2;
- R2a and R3a are independently selected from the group consisting of:
- H, —C1-4alkyl, —C2-6alkenyl, —C2-6alkynyl, —C3-8cycloalkyl, —C0-4alkylC3-8cycloalkyl, —C0-4alkylphenyl and —C0-4alkylnaphthyl, wherein from 1-4 hydrogen atoms on the ring atoms of the phenyl and naphthyl moieties may be independently replaced with a member selected from the group consisting of halo, —C1-4alkyl, —C2-6alkenyl, —C2-6alkynyl, —C3-8cycloalkyl, —C0-4alkylC3-8cycloalkyl, —CN and —NO2;
- n is an integer of 0-2;
- E is a member selected from the group consisting of:
- a direct link, —O—, —NH—, —CH2NH—, —NHCH2—, —NMe-, —NH—C(═O)—NH—, —C(═O)—NH—, —NH—C(═O)—;
- G is a member selected from the group consisting of:
- (a) a C2-alkenyl group or a C3-8-cycloalkenyl group, wherein the alkenyl group and cycloalkenyl group attachment points are the alkenyl carbon atoms and wherein the C2-alkenyl group or C3-8-cycloalkenyl group is substituted with 0-4 R1d groups;
- (b) a phenylene group wherein the ring carbon atoms of the phenylene group are substituted with 0-4 R1d groups;
- (c) a 3-8 membered a saturated, partially unsaturated or aromatic monocyclic-heterocyclic ring system containing 1-4 heteroatoms selected from N, O and S, wherein 0-4 ring atoms of the heterocyclic ring may be substituted with 0-4 R1d groups; and,
- (d) an 8-10 membered fused heterocyclic bicyclic ring system, containing 1-4 heteroatoms selected from N, O and S, wherein 0-4 ring atoms of the fused bicyclic ring system may be substituted with 0-4 R1d groups;
- R1d is a member selected from the group consisting of:
- H, halo; C1-6alkyl, carbocylic aryl, —CN; —NO2; —(CH2)0-6NR2dR3d; —SO2NR2dR3d; —SO2R2d; —CF3; —(CH2)0-6—OR2d; —OH, —OC1-6alkyl, —O—(CH2)1-6OR2d; —O—(CH2)1-6—C(═O)—O—R2d; —O—(CH2)1-6—C(═O)—N(R2d,R3d); —N(R5a)—(CH2)1-6—OR2d; —N(R5a)—(CH2)1-6—N(R2d,R3d); —C(═O)—N(R2d,R3d); —N(R5a)—(CH2)1-6—C(═O)—N(R2d,R3d); —N(—(CH2)1-6—OR2d)2; —N(R5a)—(CH2)1-6—OR2d; —N(R5a)—C(═O)—R2d; —N(R5a)—SO2R2d; —(CH2)0-6—C(═O)—O—R2d; —(CH2)0-6C(═O)—N(R2d,R3d); —(CH2)0-6—C(═NR2d)—N(R3d,R4d); —(CH2)0-6—N(R5a)C(═NR2d)—N(R3d,R4d); and a —(CH2)0-6—N(R3d) group which is attached via the nitrogen atom to a carbon atom of a 5 to 6 membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1-4 heteroatoms selected from N, O and S, and a —(CH2)0-6— group attached to a 5-6 membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1-4 heteroatoms selected from N, O and S;
- R5a, R2d, R3d and R4d are each independently a member selected from the group consisting of:
- H, C1-6-alkyl and C1-4-alkylaryl, —CN; —NO2; carbocylic aryl, —CN; —NO2; or
- R2d and R3d taken together with the N atoms there are independently attached form a 5-7 membered saturated, partially unsaturated or aromatic heterocyclic ring; or
- R3d and R4d taken together with the N atom to which they are attached form a 5-8 membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1-4 heteroatoms selected from N, O and S;
- J is a member selected from the group consisting of:
- a direct link, —O—, —NH—, —NMe-, —C(═O)—NH—, —NH—C(═O)—;
- X is a member selected from the group consisting of:
- (a) phenyl substituted with 0-3 R1e groups;
- (b) naphthyl substituted with 0-3 R1e groups and
- (c) a 6-membered aromatic heterocyclic ring system containing 1-3 N atoms and having 0-3 ring atoms substituted with 0-3 R1e groups; and
- (d) an 8-10 membered fused aromatic heterocyclic bicyclic ring system containing 1-4 heteroatoms selected from N, O and S and 0-3 ring atoms of the fused heterocyclic bicyclic ring system are substituted with 0-3 R1e groups;
- R1e is a member independently selected from the group consisting of:
- Halo; CF3; —C1-4-alkyl; carbocyclic aryl; —C0-2-alkyl-CN; —O—R2e; —C0-2-alkyl-C(═O)—O—R2e; —C0-2-alkyl-C(═O)—N(R2e, R3e); —C0-2-alkyl-NO2; —C0-2-alkyl-N(R2e, R3e); —C0-2-alkyl-SO2—N(R2e, R3e); —C0-2-alkyl-SO2—R2e; trihaloalkyl; —O—C0-2-alkyl-O—R2e; —C0-2-alkyl-O—R2e; —O—C1-4-alkyl-C(═O)—N(R2e, R3e); —O—C1-4-alkyl-C(═O)—O—R2e; —C0-2-alkyl-N(R2e)—C(═O)—R3e; —C0-2-alkyl-N(—R2e)SO2—R3e; —CH2—N(R2e)—C(═O)—R3e; —CH2—N(R2e)—SO2—R3e; —(CH2)0-6NR2eR3e; —C(═O)—N(R2e,R3e); —N(—(CH2)1-6—OR2e)2; —N(R10)—(CH2)1-6—OR2e; —N(R10)—C(═O)—R2e; —N(R10)—SO2—R2e; —C(═N(R10))—N(R2e,R3e); and a —(CH2)0-6-5-6 membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1-4 heteroatoms selected from N, O and S;
- R10, R2e and R3e are each independently a member selected from the group consisting of:
- H; —C1-4-alkyl; —C0-2-alkyl-O—R1g; —C0-2-alkyl-N(—R1g, —R2g); —C1-4-alkyl-carbocyclic aryl; —C1-4-alkyl-heterocyclic; and R10 and R2e, or R2e and R3e together with the N atom to which they are attached can form 5-8 membered heterocyclic ring containing 1-4 heteroatoms selected from N, O and S which can be substituted with 0-2 R1g groups;
- R1g and R2g are independently a member selected from the group of:
- H; halo; —C1-4-alkyl, a carbocyclic aryl group; a saturated, partially unsaturated or aromatic heterocyclic group; —CN; —C(═O)—N(R3g,R4g); —C(═O)—OR3g; —NO2; —(CH2)p—NR3gR4g; —SO2NR3gR4g; —SO2R3g; —CF3; and —(CH2)pOR3g;
- p is an integer of 0-2; and
- R3g and R4g are each independently selected from the group consisting of:
- H; C1-4-alkyl and —C0-4-alkyl-carbocyclic aryl;
A-Q-D-E-G-J-X (Ib)
where:
- A is selected from:
- (a) C1-C6-alkyl;
- (b) C3-C8-cycloalkyl;
- (c) —N(R1,R2), N(R1,R2)—C(═NR3)—, N(R1,R2)—C(═NR3)—N(R4)—, R1—C(═NR3)—, R1—C(═NR3)—N(R4)—;
- (d) phenyl, which is independently substituted with 0-2 R substituents;
- (e) naphthyl, which is independently substituted with 0-2 R substituents;
- (f) a monocyclic or fused bicyclic ring system having from 5 to 10 ring atoms, wherein 1-4 ring atoms of the ring system are selected from N, O and S, and wherein the ring system may be substituted with 0-2 R substituents;
- R is selected from:
- H, halo, —C1-4alkyl, —C2-6alkenyl, —C2-6alkynyl, —C3-8cycloalkyl, —C0-4alkylC3-8cycloalkyl, —CF3, —CN, —(CH2)m—CO2R1, —(CH2)m—C(═O)—N(R1, R2), —(CH2)m—C(═S)—N(R1, R2), —NO2, —(CH2)m—SO2N(R1, R2), —(CH2)m—SO2R1, —(CH2)mNR1R2, —(CH2)mOR1, —(CH2)m—C(═NR3)—R1, —(CH2)m—C(═NR1)—N(R1,R2), —(CH2)m—N(R4)—C(═NR3)—N(R1,R2), and a 3-8 membered cyclic system containing from 1-4 heteroatoms selected from N, O and S, wherein from 1-4 hydrogen atoms on the heterocyclic ring system may be independently replaced with a member selected from the group consisting of halo, C1-C4-alkyl, —CN—C1-4alkyl, —C2-6alkenyl, —C2-6alkynyl, —C3-8cycloalkyl, —C0-4alkylC3-8cycloalkyl and —NO2;
- m is an integer of 0-2;
- R1, R2, R3 and R4 are independently selected from the group consisting of:
- H, —(CH2)0-4OR5, —(CH2)0-4—CO2R5, —(CH2)0-4N(—R5, —R6), —C1-4alkyl, —C2-6alkenyl, —C2-6alkynyl, —C3-8cycloalkyl, —C0-4alkylC3-8cycloalkyl, —C0-4alkylaryl and —C0-4alkylheteroaryl, and a 3-8 membered cyclic system containing from 1-4 heteroatoms selected from N, O and S, wherein from 1-4 hydrogen atoms on the heterocyclic ring system may be independently replaced with a member selected from the group consisting of halo, C1-C4-alkyl, —CN—C1-4alkyl, —C2-6alkenyl, —C2-6alkynyl, —C3-8cycloalkyl, —C0-4alkylC3-8cycloalkyl and —NO2; or
- R1 and R2, or R2 and R3 taken together can form a 3-8 membered cycloalkyl or a heterocyclic ring system, wherein the heterocyclic ring system may have from 3 to 10 ring atoms, with 1 to 2 rings being in the ring system and contain from 1-4 heteroatoms selected from N, O and S, where the hydrogen atoms on the heterocyclic ring system may be independently replaced with a member selected from the group consisting of halo, C1-C4-alkyl, —CN, —CO2R5, —OH, —C1-4alkyl, —C2-6alkenyl, —C2-6alkynyl, —C3-8cycloalkyl, —C0-4alkylC3-8cycloalkyl and —NO2;
- R5 and R6 are independently selected from the group consisting of:
- H, —C1-4alkyl, —C2-6alkenyl, —C2-6alkynyl, —C3-8cycloalkyl, —C0-4alkylC3-8cycloalkyl, —C0-4alkylaryl and —C0-4alkylheteroaryl, wherein from 1-4 hydrogen atoms on the ring atoms of the phenyl and naphthyl moieties may be independently replaced with a member selected from the group consisting of halo, —C1-4alkyl, —C2-6alkenyl, —C2-6alkynyl, —C3-8cycloalkyl, —C0-4alkylC3-8cycloalkyl, —CN, and —NO2; or
- R5 and R6 taken together can form a 3-8 membered cycloalkyl or a heterocyclic ring system, wherein the heterocyclic ring system may have from 3 to 10 ring atoms, with 1 to 2 rings being in the ring system and contain from 1-4 heteroatoms selected from N, O and S, wherein from 1-4 hydrogen atoms on the heterocyclic ring system may be independently replaced with a member selected from the group consisting of halo, —C1-C4-alkyl, —CN—C1-4alkyl, —C2-6alkenyl, —C2-6alkynyl, —C3-8cycloalkyl, —C0-4alkylC3-8cycloalkyl and —NO2;
- Q is a member selected from the group consisting of:
- R7 is selected from:
- H; —C1-4-alkyl; —C0-4-alkylaryl; —C0-4-alkyl-heteroaryl; —C1-4-alkyl-O—C1-4-alkyl, —C1-4-alkyl-N(—C1-4-alkyl, —C1-4-alkyl); —C1-4-alkyl-C(═O)—O—C1-4-alkyl, and —C1-4-alkyl-C(═O)—N(—C1-4-alkyl, —C1-4-alkyl);
- D is a direct link or is a member selected from the group consisting of:
- (a) phenyl, which is independently substituted with 0-2 R1a substituents;
- (b) naphthyl, which is independently substituted with 0-2 R1a substituents; and
- (c) a monocyclic or fused bicyclic heterocyclic ring system having from 5 to 10 ring atoms, wherein 14 ring atoms of the ring system are selected from N, O and S, and wherein the ring system may be substituted from 0-2 R1a substituents;
- R1a is selected from:
- halo, —C1-4alkyl, —C2-6alkenyl, —C2-6alkynyl, —C3-8cycloalkyl, —C0-4alkylC3-8cycloalkyl, —CN, —NO2, —(CH2)nOR2a, —(CH2)nNR2aR3a, —(CH2)nCO2R2a, —(CH2)nCONR2aR3a, —SO2NR2aR3a, —SO2R2a, —CF3, and a 5-6 membered aromatic heterocyclic system containing from 1-4 heteroatoms selected from N, O and S, wherein from 1-4 hydrogen atoms on the aromatic heterocyclic system may be independently replaced with a member selected from the group consisting of halo, —C1-4alkyl, —C2-6alkenyl, —C2-6alkynyl, —C3-8cycloalkyl, —C0-4alkylC3-8cycloalkyl, —CN and —NO2:
- R2a and R3a are independently selected from the group consisting of:
- H, —C4alkyl, —C2-6alkenyl, —C2-6alkynyl, —C3-8cycloalkyl, —C0-4alkylC3-8cycloalkyl, —C0-4alkylaryl and —C0-4alkylheteroaryl, wherein from 1-4 hydrogen atoms on the ring atoms of the phenyl and naphthyl moieties may be independently replaced with a member selected from the group consisting of halo, —C1-4alkyl, —C2-6alkenyl, —C2-6alkynyl, —C3-8cycloalkyl, —C0-4alkylC3-8cycloalkyl, —CN and —NO2;
- n is an integer of 0-2;
- E is a direct link or a member selected from the group consisting of:
- R8 is a member selected from the group consisting of:
- H; —C1-4-alkyl; —C0-4-alkylaryl; —C0-4-alkyl-heteroaryl; —C1-4-alkyl-OR2b, —C1-4-alkyl-N(—R2b, —R3b); —C1-4-alkyl-C(═O)—OR2b; —C1-4-alkyl-C(═O)—N(—R2b, —R3b); —C0-4-alkyl-C(═O)—R2b; and —C0-4-alkyl-SO2—R2b;
- R2b and R3b are each a member independently selected from the group consisting of:
- H, —C1-4-alkyl, —C1-4-alkyl-CO2—C0-4-alkyl, —C0-4-alkyl-aryl; —C0-4-alkyl-heterocyclic group, and R2b and R3b together with the N atom to which they are attached can form a 5-8 membered heterocyclic ring containing 1-4 heteroatoms selected from N, O and S, wherein the heterocyclic ring may be substituted with 0-2 R1c groups;
- R1c is a member selected from the group consisting of:
- Halo; —C1-4-alkyl; —CN, —NO2; —C(═O)—N(—R2, —R3); —C(═O)—OR2c; —(CH2)q—N(—R2c, —R3c); —SO2—N(—R2c, —R3c); —SO2R2c; —CF3 and —(CH2)q—OR2c;
- R2c and R3c are each independently a member selected from the group consisting of:
- H; —C1-4-alkyl and —C1-4alkyl-aryl;
- q is an integer of 0-2;
- G is a member selected from the group consisting of:
- (a) C2-alkenyl or C3-8-cycloalkenyl, wherein the alkenyl and cycloalkenyl attachment points are the alkenyl carbon atoms and wherein the —C2-alkenyl or —C3-8-cycloalkenyl are substituted with 0-4 R1J groups;
- (b) a phenylene group wherein the ring carbon atoms of the phenylene group are substituted with 0-4 R1d groups;
- (c) a 3-8 membered a saturated, partially unsaturated or aromatic monocyclic ring system containing 1-4 heteroatoms selected from N, O and S, wherein 0-2 ring atoms of the heterocyclic ring may be substituted with 0-4 R1d groups; and,
- (d) an 8-10 membered fused cyclic system, containing 0-4 heteroatoms selected from N, O and S, wherein 0-2 ring atoms of the fused bicyclic ring system may be substituted with 0-4 R1d groups;
- R1d is a member selected from the group consisting of:
- H, halo; —CF3; —OCF3, —OCF2H, —OCFH2, —OCH2CF3, —OCF2CF3, C1-6-alkyl, carbocylic aryl, —CN; —NO2; —(CH2)0-6—NR2dR3d; —(CH2)0-6—OR2d; —OH, —OC1-6alkyl, —O—(CH2)1-6OR2d; —O—(CH2)1-6—NR2dR2d; —N(R5a)—(CH2)1-6—OR2d; —N(R5a)—(CH2)1-6—N(R2d,R3d); —(CH2)0-6—C(═O)—O—R2d; —(CH2)0-6—C(═O)—N(R2d,R3d); —O—(CH2)1-6—C(═O)—O—R2d; —O—(CH2)1-6—C(═O)—N(R2d,R3d); —N(R5a)—(CH2)1-6—C(═O)—O—R2d; —N(R5a)—(CH2)1-6—C(═O)—N(R2d,R3d); —N(—(CH2)1-6—OR2d)2; —N(—(CH2)1-6—N(R2d,R3d))2; —(CH2)0-6—SO2NR2dR3d; —(CH2)0-6—SO2R2d; —(CH2)0-6—N(R5a)—C(═O)—R2d; —(CH2)0-6—N(R5a)—SO2—R2d, —(CH2)0-6—C(═NR2d)—N(R3d,R4d); —(CH2)0-6—N(R5a)C(═NR2d)—N(R3d,R4d); —(CH2)0-6—N(R5a)C(═NR2d)—R4d; —O—(CH2)1-6—SO2NR2dR3d; —O—(CH2)1-6—SO2R2d; —O—(CH2)1-6—N(R5a)—C(═O)—R2d; —O—(CH2)1-6—N(R5a)—SO2—R2d, —O—(CH2)1-6—C(═NR2d)—N(R3d,R4d); —O—(CH2)1-6—N(R5a)C(═NR2d)—N(R3dR4d); —O—(CH2)1-6—N(R5a)C(═NR2d)—R4d; —N(R5d)—(CH2)1-6—SO2NR2dR3d; —N(R5d)—(CH2)1-6—SO2R2d; —N(R5d)—(CH2)1-6—N(R5a)—C(═O)—R2d; —N(R5d)—(CH2)1-6—N(R5a)—SO2—R2d, —N(R5d)—(CH2)1-6—C(═NR2d)—N(R3d,R4d); —N(R5d)—(CH2)1-6—N(R5a)C(═NR2d)—N(R3d,R4d); —N(R5d)—(CH2)1-6—N(R5a)C(═NR2d)—R4d; and a 3-8 membered cyclic system containing from 1-4 heteroatoms selected from N, O and S, wherein from 1-4 hydrogen atoms on the heterocyclic ring system may be independently replaced with a member selected from the group consisting of halo, C1-C4-alkyl, —CN—C1-4alkyl, —C2-6alkenyl, —C2-6alkynyl, —C3-8cycloalkyl, —C0-4alkylC3-8cycloalkyl and —NO2;
- R5a, R2d, R3d, R4d and R5d are each independently a member selected from the group consisting of:
- H, C1-6-alkyl and C1-6-alkylaryl, —CN; —NO2; or
- R2d and R3d, or R3d and R4d taken together with the N atoms they are independently attached form a 3-8 membered saturated, partially unsaturated or aromatic heterocyclic ring;
- J is a direct link or is a member selected from the group consisting of:
- R9 is a member selected from the group consisting of:
- H; —C1-4-alkyl; —C0-4-alkylaryl; —C0-4-alkyl-heteroaryl; —C1-4-alkyl-OR6a, —C1-4-alkyl-N(—R6a, —R6b); —C1-4-alkyl-C(═O)—OR6a, and —C1-4-alkyl-C(═O)—N(R6a, R6b);
- R6a and R6b are each a member independently selected from the group consisting of:
- H and —C1-6-alkyl;
- X is a member selected from the group consisting of:
- (a) phenyl substituted with 0-3 R1e groups;
- (b) naphthyl substituted with 0-3 R1e groups and
- (c) a 6-membered aromatic heterocyclic ring system containing 1-3 N atoms and having 0-3 ring atoms substituted with 0-3 R1e groups; and
- (d) an 8-10 membered fused bicyclic ring system containing 1-4 heteroatoms selected from N, O and S and 0-3 ring atoms of the fused heterocyclic bicyclic ring system are substituted with 0-3 R1e groups;
- R1e is a member independently selected from the group consisting of:
- Halo; CF3; —C1-4-alkyl; carbocyclic aryl; —C0-2-alkyl-CN; —O—R2e; —C0-2-alkyl-C(═O)—O—R2e; —C0-2-alkyl-C(═O)—N(R2e, R3e); —C0-2-alkyl-NO2; —C0-2-alkyl-N(R2e, R3e); —C0-2-alkyl-SO2—N(R2e, R3e); —C0-2-alkyl-SO2—R2e; trihaloalkyl; —O—C0-2-alkyl-O—R2e; —C0-2-alkyl-O—R2e; —O—C1-4-alkyl-C(═O)—N(R2e, R3e); —O—C1-4-alkyl-C(═O)—O—R2e; —C0-2-alkyl-N(R2e)—C(═O)—R3e; —C0-2-alkyl-N(—R2e)—SO2—R2e; —CH2—N(R2e)—C(═O)—R3e; —CH2—N(R2e)—SO2—R3e; —(CH2)0-6—NR2eR3e; —C(═O)—N(R2e,R3e); —N(—(CH2)1-6—OR2e)2; —N(R10)—(CH2)1-6—OR2e; —N(R10)—C(═O)—R2e; —N(R10)—SO2—R2e; —C(═N(R10))—N(R2e,R3e); and a —(CH2)0-6-5-6 membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1-4 heteroatoms selected from N, O and S;
- R10, R2e and R3e are each independently a member selected from the group consisting of:
- H; —C1-4-alkyl; —C0-2-alkyl-O—R1g; —C0-2-alkyl-N(—R1g, —R2g); —C1-4-alkyl-carbocyclic aryl; —C1-4-alkyl-heterocyclic; and R10 and R2e, or R2e and R3e together with the N atom to which they are attached can form 5-8 membered heterocyclic ring containing 1-4 heteroatoms selected from N, O and S which can be substituted with 0-2 R1g groups;
- R1g and R2g are independently a member selected from the group of:
- H; halo; —C1-4-alkyl, a carbocyclic aryl group; a saturated, partially unsaturated or aromatic heterocyclic group; —CN; —C(—O)—N(R3g)R4g; —C(═O)—OR3g; —NO2; —(CH2)p—NR3gR4g; —SO2NR3gR4g; —SO2R3g; —CF3; and —(CH2)pOR3g;
- p is an integer of 0-2;
- R3g and R4g are each independently selected from the group consisting of:
- H; C1-4-alkyl and —C0-4-alkyl-carbocyclic aryl;
A-Q-D-E-G-J-X (Ic)
where:
- A is a member selected from the group consisting of:
- Q is a member selected from the group consisting of:
- D is a direct link or is a member selected from the group consisting of:
- E is a member selected from the group consisting of:
- a direct link, —CH2NH—, —C(═O)—NH—, —NH—C(═O)—;
- G is a member selected from the group consisting of:
- G is substituted by 0-4 R1d groups and each R1d group is independently selected from the group consisting of:
- H, —CH3, —CF3, —Cl, —F, —Br, —NH2, —NMe2, —OH, —OMe, —NHSO2Me, —NO2, —CN, —C(═O)—OMe, —CO2H, —CONH2, —SO2NH2, —SO2CH3, —NHC(═O)Me, —C(═O)N(-Me)2, —CH2NH2, —CH2N(-Me)2, —CH2OH, —OCH2CO2H, —OCH2C(═O)—OMe, —OCH2C(═O)—NH2 and —OCH2C(═O)N(-Me)2.
- J is a member selected from the group consisting of:
- a direct link, —O—, —NH—, —C(═O)—NH— and —NH—C(═O)—;
- X is a member selected from the group consisting of:
- R1a is a member selected from the group consisting of:
- H, —F, —Cl and —Br;
- R1e is a member selected from the group consisting of:
- H, —F, —Cl, —Br, —OMe, —OH, -Me, —CF3 and —CH2NH2; and
- A-Q is a member selected from the group consisting of:
- R1a is a member selected from the group consisting of:
- H, —F, —Cl and —Br;
- R1e is a member selected from the group consisting of:
- H, —F, —Cl, —Br, —OMe, —OH, -Me, —CF3 and —CH2NH2; and
- A-Q is a member selected from the group consisting of:
- R1a is a member selected from the group consisting of:
- H, —F, —Cl and —Br;
- R1e is a member selected from the group consisting of:
- H, —F, —Cl, —Br, —OMe, —OH, -Me, —CF3 and —CH2NH2;
- A-Q is a member selected from the group consisting of:
- R1e is a member selected from the group consisting of:
- H, —F, —Cl, —Br, —OMe, —OH, -Me, —CF3 and —CH2NH2;
- A-Q is a member selected from the group consisting of
- D is a member selected from the group consisting of:
- J is a member selected from the group consisting of:
- —NHC(═O)—, —C(═O)NH—;
- X is a member selected from the group consisting of:
- R is a member selected from the group of:
- —SO2—NH2 and —SO2Me;
- R1a is a member selected from the group of:
- H, —F, —Cl and Br;
- E is a member selected from the group consisting of:
- —NHC(═O)— and —C(═O)NH—;
- R1d1, R1d2, and R1d4 are independently a member selected from the group of:
- H, —F, —Cl, —Br, -Me, —NO2, —OH, —OMe, —NH2, —NHAc, —NHSO2Me, —CH2OH and —CH2NH2;
- R1d3 is a member selected from the group of:
- H, —CH3, —CF3, —Cl, —F, —Br, —NH2, —N(-Me)2, —OH, —OMe, —NHSO2Me, —NO2, —CN, —C(═O)—OMe, —CO2H, —C(═O)—NH2, —SO2NH2, —SO2CH3, —NHC(═O)-Me, —C(═O)—N(-Me)2, —CH2NH2, —CH2—N(-Me)2, —CH2OH, —OCH2CO2H, —OCH2C(═O)—OMe, —OCH2C(═O)—NH2, and —OCH2C(═O)—N(-Me)2,
- R1e is a member selected from the group of:
- F, —Cl, —Br, —OH, -Me and —OMe,
- R is a member selected from the group consisting of:
- —SO2NH2, —SO2Me;
- R1a is a member selected from the group consisting of:
- H, —F, —Cl and Br;
- R1e is a member selected from the group consisting of:
- H, —F, —Cl, —Br, —OMe, —OH, -Me, —CF3 and —CH2NH2; and
- G is a member selected from the group consisting of:
wherein each G group may be substituted by 0-4 R1d groups and each such R1d group is independently selected from the group consisting of:
-
- H, —CH3, —CF3, —Cl, —F, —Br, —NH2, —N(-Me)2, —OH, —OMe, —NHSO2Me, —NO2, —CN, —C(═O)—OMe, —CO2H, —C(═O)—NH2, —SO2NH2, —SO2CH3, —NH—C(═O)-Me, —C(═O)—N(-Me)2, —CH2NH2, —CH2—N(-Me)2, —CH2OH, —OCH2CO2H, —OCH2CO2Me, —OCH2C(═O)—NH2, —OCH2C(═O)—N(-Me)2.
- J-X are collectively a member selected from the group consisting of:
- R is a member selected from the group of:
- —SO2NH2, and —SO2Me;
- R1a is a member selected from the group of:
- H, —F, —Cl and Br;
- E is a member selected from the group consisting of:
- —NHC(═O)— and —C(═O)NH—;
- J is a member selected from the group consisting of:
- —NHC(═O)— and —C(═O)NH—, O;
- R1d1, R1d2, and R1d4 are independently a member selected from the group of:
- H, —F, —Cl, —Br, -Me, —NO2, —OH, —OMe, —NH2, —NHAc, —NHSO2Me, —CH2OH, —CH2NH2;
- R1d3 is a member selected from the group of:
- H, —CH3, —CF3, —Cl, —F, —Br, —NH2, —N(-Me)2, —OH, —OMe, —NHSO2Me, —NO2, —CN, —CO2Me, —CO2H, —C(═O)—NH2, —SO2NH2, —SO2CH3, —NHC(═O)-Me, —C(═O)—N(-Me)2, —CH2NH2, —CH2—N(-Me)2, —CH2OH, —OCH2CO2H, —OCH2C(═O)—OMe, —OCH2C(═O)—NH2, —OCH2C(═O)—N(-Me)2
- R13 is a member selected from the group of:
- F, —Cl, —Br, —OH, -Me and —OMe;
- R is a member selected from the group of:
- —SO2—NH2, and —SO2Me;
- R1a is a member selected from the group of:
- H, —F, —Cl and Br;
- R1d is a member selected from the group consisting of:
- —H, —CH3, —CF3, —CN, —SO2NH2 and —SO2CH3; and
- R1e is a member selected from the group of:
- —Cl and —Br;
- A-Q taken together are a member selected from the group consisting of:
- A-Q is a member selected from the group of:
- R1a is a member selected from the group of:
- H, —F, —Cl and Br;
- R1d1, R1d2, and R1d4 are independently a member selected from the group of:
- H, —F, —Cl, —Br, -Me, —NO2, —OH, —OMe, —NH2, —NHAc, —NHSO2Me, —CH2OH, —CH2NH2
- R1d3 is a member selected from the group of:
- R1e is a member selected from the group of:
- F, —Cl, —Br, —OH, -Me and —OMe;
and all pharmaceutically acceptable isomers, salts, hydrates, solvates and prodrug derivatives thereof.
In formula VI:
and all pharmaceutically acceptable isomers, salts, hydrates, solvates and prodrug derivatives thereof.
In formula VII:
- where Z′ is as described above;
- R1a is a member selected from the group of H, —F, —Cl and Br;
- R1d2 and R1d4 are each H;
- R1d1 is R1d3 are each independently a member selected from the group of H, —Cl, —F, —Br, —OH and —OMe;
- R1e is a member selected from the group of —F, —Cl, —Br, —OH, -Me and —OMe.
Examples of suitable compounds of formula VII, as described above, include, but are not limited to:
- Q is a member selected from the group consisting of:
- a direct link, —CH2—, —C(═O)—, —NH—, —N(Me)—, —NHCH2—, —N(Me)CH2—, —C(═NH)—, —C(═NMe)-;
- D is a direct link or is a member selected from the group consisting of:
- E is a member selected from the group consisting of:
- a direct link, —CH2NH—, —NHCH2—, —CH2O—, —OCH2—, —CH2NH—, —CONH—, —NHCO—, —CONMe-, —NMeCO—;
- G is a member selected from the group consisting of:
- G is substituted by 0-4 R1d groups and each R1d group is independently selected from the group consisting of:
- H, -Me, —F, —Cl, —Br, aryl, heteroaryl, —NH2, —NMe2, —NHMe, —NHSO2Me, —NHCOMe, —CH3, —CF3, —OH, —OCH3, —SCH3, —OCF3, —OCH2F, —OCHF2, —OCH2CF3, —OCF2CF3, —NO2, —CN, —CO2H, —CO2Me, —CO2Et, —CONH2, —CONHMe, —CONMe2, —SO2NH2, —SO2CH3, —SO2NMe2, —CH2OH, —CH2NH2, —CH2NHMe, —CH2NMe2, —OCH2CO2H, —OCH2CO2Me, —OCH2CO2Et, —OCH2CONH2, —OCH2CONMe2, —OCH2CONHMe, —OCH2CH2OMe, —OCH2CH2OEt, —OCH2CH2NH2, —OCH2CH2NHMe, —OCH2CH2NMe2, —NHCH2CH2OMe, —SCH2CH2OMe, —SO2CH2CH2OMe, —OCH2CH2SO2Me, —NHCH2CH2NHMe, —NHCH2CH2NMe2, —N(CH2CH2OH)2, —N(CH2CH2OMe)2, —NHCH2CO2H, —NHCH2CO2Et, —NHCH2CO2Et, —NHCH2CONH2, —NHCH2CONMe2, —NHCH2CONHMe, —N(CH3)CH2CO2H, —N(CH3)CH2CO2Et, —(NMe)CH2COOH, —N(Me)CH2CONH2, —N(Me)CH2CH2NMe2, —N(Me)CH2CH2OMe, —NHCH2CH2OMe,
- J is a member selected from the group consisting of:
- a direct link, —SO2—, —CO—, —O—, —NH—, —C(═O)—NH— and —NH—C(═O)—;
- X is a member selected from the group consisting of:
and all pharmaceutically acceptable isomers, salts, hydrates, solvates and prodrug derivatives thereof.
- R1a is a member selected from the group consisting of:
- H, —F, —Cl and —Br;
- R1e is a member selected from the group consisting of:
- H, —F, —Cl, —Br, —OMe, —OH, -Me, —CF3 and —CH2NH2; and
- A-Q is a member selected from the group consisting of:
and all pharmaceutically acceptable isomers, salts, hydrates, solvates and prodrug derivatives thereof.
- R is a member selected from the group consisting of:
- —SO2Me, —SO2NH2, —CH2NH2, —CH2N(CH3)2;
- R1a is a member selected from the group consisting of:
- H, —F;
- R1d1 is a member selected from the group consisting of:
- H, -Me, —F, —Cl, —Br, aryl, heteroaryl, —NH2, —NMe2, —NHMe, —NHSO2Me, —NHCOMe, —CH3, —CF3, —OH, —OCH3, —SCH3, —OCF3, —OCH2F, —OCHF2, —OCH2CF3, —OCF2CF3, —NO2, —CN, —CO2H, —CO2Me, —CO2Et, —CONH2, —CONHMe, —CONMe2, —SO2NH2, —SO2CH3, —SO2NMe2, —CH2OH, —CH2NH2, —CH2NHMe, —CH2NMe2, —OCH2CO2H, —OCH2CO2Me, —OCH2CO2Et, —OCH2CONH2, —OCH2CONMe2, —OCH2CONHMe, —OCH2CH2OMe, —OCH2CH2OEt, —OCH2CH2NH2, —OCH2CH2NHMe, —OCH2CH2NMe2, —NHCH2CH2OMe, —SCH2CH2OMe, —SO2CH2CH2OMe, —OCH2CH2SO2Me, —NHCH2CH2NHMe, —NHCH2CH2NMe2, —N(CH2CH2OH)2, —N(CH2CH2OMe)2, —NHCH2CO2H, —NH2CO2Et, —NHCH2CO2Et, —NHCH2CONH2, —NHCH2CONMe2, —NHCH2CONHMe, —N(CH3)CH2CO2H, —N(CH3)CH2CO2Et, —(NMe)CH2COOH, —N(Me)CH2CONH2, —N(Me)CH2CH2NMe2, —N(Me)CH2CH2OMe, —NHCH2CH2OMe,
and all pharmaceutically acceptable isomers, salts, hydrates, solvates and prodrug derivatives thereof.
- A-Q is a member selected from the group consisting of:
- R1a is a member selected from the group consisting of:
- H, —F;
- R1d1 is a member selected from the group consisting of:
- H, -Me, —F, —Cl, —Br, aryl, heteroaryl, —NH2, —NMe2, —NHMe, —NHSO2Me, —NHCOMe, —CH3, —CF3, —OH, —OCH3, —SCH3, —OCF3, —OCH2F, —OCHF2, —OCH2CF3, —OCF2CF3, —NO2, —CN, —CO2H, —CO2Me, —CO2Et, —CONH2, —CONHMe, —CONMe2, —SO2NH2, —SO2CH3, —SO2NMe2, —CH2OH, —CH2NH2, —CH2NHMe, —CH2NMe2, —OCH2CO2H, —OCH2CO2Me, —OCH2CO2Et, —OCH2CONH2, —OCH2CONMe2, —OCH2CONHMe, —OCH2CH2OMe, —OCH2CH2OEt, —OCH2CH2NH2, —OCH2CH2NHMe, —OCH2CH2NMe2, —NHCH2CH2OMe, —SCH2CH2OMe, —SO2CH2CH2OMe, —OCH2CH2SO2Me, —NHCH2CH2NHMe, —NHCH2CH2NMe2, —N(CH2CH2OH)2, —N(CH2CH2OMe)2, —NHCH2CO2H, —NHCH2CO2Et, —NHCH2CO2Et, —NHCH2CONH2, —NHCH2CONMe2, —NHCH2CONHMe, —N(CH3)CH2CO2H, —N(CH3)CH2CO2Et, —(NMe)CH2COOH, —N(Me)CH2CONH2, —N(Me)CH2CH2NMe2, —N(Me)CH2CH2OMe, —NHCH2CH2OMe,
and all pharmaceutically acceptable isomers, salts, hydrates, solvates and prodrug derivatives thereof
- A-Q is a member selected from the group consisting of:
- R1a is a member selected from the group consisting of:
- H, —F;
- R1e is a member selected from the group consisting of:
- H, —F, —SO2Me, —SO2NH2, —CN, —CONH2, —CH2NH2, —CH2NMe2;
- R1d3 is a member selected from the group consisting of:
- H, -Me, —F, —Cl, —Br, aryl, heteroaryl, —NH2, —NMe2, —NHMe, —NHSO2Me, —NHCOMe, —CH3, —CF3, —OH, —OCH3, —SCH3, —OCF3, —OCH2F, —OCHF2, —OCH2CF3, —OCF2CF3, —NO2, —CN, —CO2H, —CO2Me, —CO2Et, —CONH2, —CONHMe, —CONMe2, —SO2NH2, —SO2CH3, —SO2NMe2, —CH2OH, —CH2NH2, —CH2NHMe, —CH2NMe2, —OCH2CO2H, —OCH2CO2Me, —OCH2CO2Et, —OCH2CONH2, —OCH2CONMe2, —OCH2CONHMe, —OCH2CH2OMe, —OCH2CH2OEt, —OCH2CH2NH2, —OCH2CH2NHMe, —OCH2CH2NMe2, —NHCH2CH2OMe, —SCH2CH2OMe, —SO2CH2CH2OMe, —OCH2CH2SO2Me, —NHCH2CH2NHMe, —NHCH2CH2NMe2, —N(CH2CH2OH)2, —N(CH2CH2OMe)2, —NHCH2CO2H, —NHCH2CO2Et, —NHCH2CO2Et, —NHCH2CONH2, —NHCH2CONMe2, —NHCH2CONHMe, —N(CH3)CH2CO2H, —N(CH3)CH2CO2Et, —(NMe)CH2COOH, —N(Me)CH2CONH2, —N(Me)CH2CH2NMe2, —N(Me)CH2CH2OMe, —NHCH2CH2OMe,
and all pharmaceutically acceptable isomers, salts, hydrates, solvates and prodrug derivatives thereof.
- A-Q is a member selected from the group consisting of:
- R1a is a member selected from the group consisting of:
- H, —F;
- R1e is a member selected from the group consisting of:
- —Cl, —Br;
- R1d3 is a member selected from the group consisting of:
- H, F, Cl, Br, —OCH3, —OCF3, —OCH2F, —OCHF2, —OCH2CF3, —OCF2CF3;
and all pharmaceutically acceptable isomers, salts, hydrates, solvates and prodrug derivatives thereof.
- H, F, Cl, Br, —OCH3, —OCF3, —OCH2F, —OCHF2, —OCH2CF3, —OCF2CF3;
- A-Q is a member selected from the group consisting of:
- R1a is a member selected from the group consisting of:
- H, —F;
- R1d3 is a member selected from the group consisting of:
- H, —F, —Cl, —Br, —OCH3, —OCF3, —OCH2F, —OCHF2, —OCH2CF3, —OCF2CF3, —NHSO2Me, —NHAc, —SO2Me, —SO2NH2;
- X is a member selected from the group consisting of:
and all pharmaceutically acceptable isomers, salts, hydrates, solvates and prodrug derivatives thereof.
- A-Q is a member selected from the group consisting of:
- R1a is a member selected from the group consisting of:
- H, —F;
and all pharmaceutically acceptable isomers, salts, hydrates, solvates and prodrug derivatives thereof.
- H, —F;
- R1a is a member selected from the group consisting of:
- H, —F;
- R1d1 is a member selected from the group consisting of:
- H, —OMe;
- R1d3 is a member selected from the group consisting of:
- H, —F, —Cl, —Br, —OMe, —OCF3;
- R1e is a member selected from the group consisting of:
- H, —F, —Cl, —Br;
- A-Q is a member selected from the group consisting of:
and all pharmaceutically acceptable isomers, salts, hydrates, solvates and prodrug derivatives thereof.
- D is a member selected from the group consisting of:
and all pharmaceutically acceptable isomers, salts, hydrates, solvates and prodrug derivatives thereof.
- R1d1 is H or —OMe;
- A-Q-D is a member selected from the group consisting of:
and all pharmaceutically acceptable isomers, salts, hydrates, solvates and prodrug derivatives thereof.
- R1a is H or F;
- R1d1 is H or —OMe;
- A-Q is a member selected from the group consisting of:
and all pharmaceutically acceptable isomers, salts, hydrates, solvates and prodrug derivatives thereof.
- R1a is H or F;
- R1d1 is H or —OMe;
- A-Q is a member selected from the group consisting of:
- R1a is a member selected from the group consisting of: H, —F,
and all pharmaceutically acceptable isomers, salts, hydrates, solvates and prodrug derivatives thereof.
- R1a is H or F;
- R1d1 is H or —OMe; and
- A-Q is a member selected from the group consisting of:
and all pharmaceutically acceptable isomers, salts, hydrates, solvates and prodrug derivatives thereof.
- A-Q is a member selected from the group consisting of:
and all pharmaceutically acceptable isomers, salts, hydrates, solvates and prodrug derivatives thereof.
- R1a is H or F;
- R1d1 is H or —OMe;
- A-Q is a member selected from the group consisting of:
- and X is a member selected from the group consisting of:
and all pharmaceutically acceptable isomers, salts, hydrates, solvates and prodrug derivatives thereof.
- R1a is H or F;
- A-Q is a member selected from the group consisting of:
- R1d1 is a member selected from the group consisting of:
- H, —F, —Cl, —Br, aryl, heteroaryl, —NH2, —NMe2, —NHMe, —NHSO2Me, —NHCOMe, —CH3, —CF3, —OH, —OCH3, —SCH3, —OCF3, —OCH2F, —OCHF2, —OCH2CF3, —OCF2CF3, —NO2, —CN, —CO2H, —CO2Me, —CO2Et, —CONH2, —CONHMe, —CONMe2, —SO2NH2, —SO2CH3, —SO2NMe2, —CH2OH, —CH2NH2, —CH2NHMe, —CH2NMe2, —OCH2CO2H, —OCH2CO2Me, —OCH2CO2Et, —OCH2CONH2, —OCH2CONMe2, —OCH2CONHMe, —OCH2CH2OMe, —OCH2CH2OEt, —OCH2CH2NH2, —OCH2CH2NHMe, —OCH2CH2NMe2, —NHCH2CH2OMe, —SCH2CH2OMe, —SO2CH2CH2OMe, —OCH2CH2SO2Me, —NHCH2CH2NHMe, —NHCH2CH2NMe2, —N(CH2CH2OH)2, —N(CH2CH2OMe)2, —NHCH2CO2H, —NHCH2CO2Et, —NHCH2CO2Et, —NHCH2CONH2, —NHCH2CONMe2, —NHCH2CONHMe, —N(CH3)CH2CO2H, —N(CH3)CH2,CO2Et, —(NMe)CH2COOH, —N(Me)CH2CONH2, —N(Me)CH2CH2NMe2, —N(Me)CH2CH2OMe, —NHCH2CH2OMe,
- R1d3 is a member selected from the group consisting of:
- H, —F, —Cl, —Br, —OCH3, —OCF3, —OCH2F, —OCHF2, —OCH2CF3, —OCF2CF3; and
- X is a member selected from the group consisting of:
and all pharmaceutically acceptable isomers, salts, hydrates, solvates and prodrug derivatives thereof.
- A-Q is a member selected from the group consisting of:
and all pharmaceutically acceptable isomers, salts, hydrates, solvates and prodrug derivatives thereof.
- A-Q is a member selected from the group consisting of:
and all pharmaceutically acceptable isomers, salts, hydrates, solvates and prodrug derivatives thereof.
- R1a is H or F;
- A-Q is a member selected from the group consisting of:
- R1d1 is a member selected from the group consisting of: H, OMe, Cl, F, OCF3,
and all pharmaceutically acceptable isomers, salts, hydrates, solvates and prodrug derivatives thereof.
- R1a is H or F;
- A-Q is a member selected from the group consisting of:
- R1d1 is a member selected from the group consisting of:
- H, —F, —Cl, —Br, —OMe, —OCF3, —OH, —NMe2, —OCH2CO2Et, —OCH2CO2H;
- R1d3 is a member selected from the group consisting of:
- H, —F, —Cl, —Br, —OMe, —OCF3, —OH, —NMe2, —OCH2CO2Et, —OCH2CO2H, —OCF2H, —OCFH2, —OCF2CF3, —OCH2CH3,
and all pharmaceutically acceptable isomers, salts, hydrates, solvates and prodrug derivatives thereof.
- R1a is H or F;
- A-Q is a member selected from the group consisting of:
- R1d1 is a member selected from the group consisting of:
- H, —F, —Cl, —Br, —OMe, —OCF3, —OH, —NMe2, —OCH2CO2Et, —OCH2CO2H
- R1d3 is a member selected from the group consisting of:
- H, —F, —Cl, —Br, —OMe, —OCF3, —OH, —NMe2, —OCH2CO2Et, —OCH2CO2H, —OCF2H, —OCFH2, —OCF2CF3, —OCH2CH3,
and all pharmaceutically acceptable isomers, salts, hydrates, solvates and prodrug derivatives thereof.
- H, —F, —Cl, —Br, —OMe, —OCF3, —OH, —NMe2, —OCH2CO2Et, —OCH2CO2H, —OCF2H, —OCFH2, —OCF2CF3, —OCH2CH3,
- R1a is H or F;
- R1d1 is selected from H, —OMe, —NMe2,
- R1d3 is Cl or Br;
- A-Q is a member selected from the group consisting of:
and all pharmaceutically acceptable isomers, salts, hydrates, solvates and prodrug derivatives thereof.
- R1a is H or F;
- R1d1 is selected from H, —OMe, —NMe2,
- R1d3 is Cl or Br;
- A-Q is a member selected from the group consisting of:
and all pharmaceutically acceptable isomers, salts, hydrates, solvates and prodrug derivatives thereof.
- R1a is H or F;
- R1d1 is selected from H, —OMe, —NMe2,
- A-Q is a member selected from the group consisting of:
and all pharmaceutically acceptable isomers, salts, hydrates, solvates and prodrug derivatives thereof.
- R1a is H or F;
- R1d1 is selected from H, —OMe, —NMe2,
- A-Q is a member selected from the group consisting of:
and all pharmaceutically acceptable isomers, salts, hydrates, solvates and prodrug derivatives thereof.
- R1a is H or F;
- R1d1 is selected from H, —OMe, —NMe2,
- A-Q is a member selected from the group consisting of:
and all pharmaceutically acceptable isomers, salts, hydrates, solvates and prodrug derivatives thereof.
- R1a is H or F;
- R1d1 is selected from H, —OMe, —NMe2,
- A-Q is a member selected from the group consisting of:
and all pharmaceutically acceptable isomers, salts, hydrates, solvates and prodrug derivatives thereof.
- A-Q is a member selected from the group consisting of:
- R1a is a member selected from the group consisting of:
- H, —F, —Cl and Br;
- R1e is a member selected from the group consisting of:
- H, —F, —Cl, —Br, —OMe, —OH, -Me, —CF3 and —CH2NH2; and
- G is a member selected from the group consisting of:
wherein each G group is substituted by 0-4 R1d groups and each such R1d group is independently selected from the group consisting of:
-
- H, -Me, —F, —Cl, —Br, aryl, heteroaryl, —NH2, —NMe2, —NHMe, —NHSO2Me, —NHCOMe, —CH3, —CF3, —OH, —OCH3, —SCH3, —OCF3, —OCH2F, —OCHF2, —OCH2CF3, —OCF2CF3, —NO2, —CN, —CO2H, —CO2Me, —CO2Et, —CONH2, —CONHMe, —CONMe2, —SO2NH2, —SO2CH3, —SO2 NMe2, —CH2OH, —CH2NH2, —CH2NHMe, —CH2NMe2, —OCH2CO2H, —OCH2CO2Me, —OCH2CO2Et, —OCH2CONH2, —OCH2CONMe2, —OCH2CONHMe, —OCH2CH2OMe, —OCH2CH2OEt, —OCH2CH2NH2, —OCH2CH2NHMe, —OCH2CH2NMe2, —NHCH2CH2OMe, —SCH2CH2OMe, —SO2CH2CH2OMe, —OCH2CH2SO2Me, —NHCH2CH2NHMe, —NHCH2CH2NMe2, —N(CH2CH2OH)2, —N(CH2CH2OMe)2, —NHCH2CO2H, —NHCH2CO2Et, —NHCH2CO2Et, —NHCH2CONH2, —NHCH2CONMe2, —NHCH2CONHMe, —N(CH3)CH2CO2H, —N(CH3)CH2CO2Et, —(NMe)CH2COOH, —N(Me)CH2CONH2, —N(Me)CH2CH2NMe2, —N(Me)CH2CH2OMe, —NHCH2CH2OMe,
and all pharmaceutically acceptable isomers, salts, hydrates, solvates and prodrug derivatives thereof.
- R1a is a member selected from the group of:
- H, —F, —Cl, —Br;
- R1d is a member selected from the group of:
- H, —F, —Cl, —Br, —OMe;
- R1e1 is a member selected from the group of:
- H, —F, —Cl, —Br, —NH2, —CH2NH2, —OMe, —OH, —CN, —SO2Me, —SO2NH2; and
- R1e2 is a member selected from the group of:
- H, —F, —Cl, —Br, —NH2,
and all pharmaceutically acceptable isomers, salts, hydrates, solvates and prodrug derivatives thereof.
- H, —F, —Cl, —Br, —NH2,
- A-Q is a member selected from the group of:
- R1a is a member selected from the group of:
- H, —F, —Cl and Br; and
- R1d is a member selected from the group of:
- H, —F, —Cl, —Br, —OMe,
and all pharmaceutically acceptable isomers, salts, hydrates, solvates and prodrug derivatives thereof.
- H, —F, —Cl, —Br, —OMe,
- A-Q is a member selected from the group of:
- R1a is a member selected from the group of:
- H, —F, —Cl and Br; and
- R1e is a member selected from the group of:
- H, —F, —Cl, —Br, —NH2, —CH2NH2, —OMe, —OH, —CN, —SO2Me, —SO2NH2.
and all pharmaceutically acceptable isomers, salts, hydrates, solvates and prodrug derivatives thereof.
- H, —F, —Cl, —Br, —NH2, —CH2NH2, —OMe, —OH, —CN, —SO2Me, —SO2NH2.
- R is a member selected from the group of:
- —SO2NH2, —SO2Me, —CH2NMe2;
- R1a is a member selected from the group of:
- H, —F, —Cl, —Br;
- R1d is a member selected from the group of:
- H, —F, —Cl, —Br, —CN, CF3, —CH3, —SO2NH2, —SO2Me; and
- R1e is a member selected from the group of:
- —Cl, —Br,
and all pharmaceutically acceptable isomers, salts, hydrates, solvates and prodrug derivatives thereof.
- —Cl, —Br,
- A-Q taken together are a member selected from the group consisting of:
and all pharmaceutically acceptable isomers, salts, hydrates, solvates and prodrug derivatives thereof.
- A-Q is a member selected from the group consisting of:
- R1a is a member selected from the group consisting of:
- H, —F, —Cl and Br;
- G is a member selected from the group consisting of:
wherein each G group is substituted by 0-4 R1d groups and each such R1d group is independently selected from the group consisting of:
-
- H, -Me, —F, —Cl, —Br, aryl, heteroaryl, —NH2, —NMe2, —NH Me, —NHSO2Me, —NHCOMe, —CH3, —CF3, —OH, —OCH3, —SCH3, —OCF3, —OCH2F, —OCHF2, —OCH2CF3, —OCF2CF3, —NO2, —CN, —CO2H, —CO2Me, —CO2Et, —CONH2, —CONHMe, —CONMe2, —SO2NH2, —SO2CH3, —SO2NMe2, —CH2OH, —CH2NH2, —CH2NHMe, —CH2NMe2, —OCH2CO2H, —OCH2CO2Me, —OCH2CO2Et, —OCH2CONH2, —OCH2CONMe2, —OCH2CONHMe, —OCH2CH2OMe, —OCH2CH2OEt, —OCH2CH2NH2, —OCH2CH2NHMe, —OCH2CH12NMe2, —NHCH2CH2OMe, —SCH2CH2OMe, —SO2CH2CH2OMe, —OCH2CH2SO2Me, —NHCH2CH2NHMe, —NHCH2CH2NMe2, —N(CH2CH2OH)2, —N(CH2CH2OMe)2, —NHCH2CO2H, —NHCH2CO2Et, —NHCH2CO2Et, —NHCH2CONH2, —NHCH2CONMe2, —NHCH2CONHMe, —N(CH3)CH2CO2H, —N(CH3)CH2CO2Et, —(NMe)CH2COOH, —N(Me)CH2CONH2, —N(Me)CH2CH2NMe2, —N(Me)CH2CH2OMe, —NHCH2CH2OMe,
- J is a member selected from the group consisting of:
- —CONH—, —NHCO—, —O—, —NH—, —NMe-, —CONMe-, —NMeCO—; and
- X is a member selected from the group consisting of:
and all pharmaceutically acceptable isomers, salts, hydrates, solvates and prodrug derivatives thereof.
- A-Q is a member selected from the group of:
- R1a is a member selected from the group of:
- H, —F, —Cl, —Br;
- R1d1, R1d2, R1d3 and R1d4 is independently a member selected from the group of:
- H, —F, —Cl, —Br, —NO2, —NH2, —NHMe, —NMe2, —NHAc, —NHSO2Me, —SO2Me, —CO2H, —CO2Me, —OH, —OMe, —N(Me)CO2H, —N(Me)CO2Et and
- R1e is a member selected from the group of:
- H, —OH,
and all pharmaceutically acceptable isomers, salts, hydrates, solvates and prodrug derivatives thereof.
- H, —OH,
- R is a member selected from the group of:
- —SO2Me, —SO2NH2, —CH2NH2, —CH2N(CH3)2;
- R1a is a member selected from the group of:
- H, —F;
- R1d2 and R1d3 is independently a member selected from the group of:
- H, —F, —Cl, —Br, —NO2; —NH2, —NHMe, —NMe2, —NHAc, —NHSO2Me, —SO2Me, —CO2H, —CO2Me, —OH, —OMe; and
- R1e is a member selected from the group of:
- H, —OH,
and all pharmaceutically acceptable isomers, salts, hydrates, solvates and prodrug derivatives thereof.
- H, —OH,
- R is a member selected from the group of:
- —SO2Me, —SO2NH2, —CH2NH2, —CH2N(CH3)2;
- R1a is a member selected from the group of:
- H, —F;
- R1d2 and R1d3 is independently a member selected from the group of:
- H, —F, —Cl, —Br, —NO2, —NH2, —NHMe, —NMe2, —NHAc, —NHSO2Me, —SO2Me, —CO2H, —CO2Me, —OH, —OMe; and
- R1e is a member selected from the group of:
- H, —OH,
and all pharmaceutically acceptable isomers, salts, hydrates, solvates and prodrug derivatives thereof.
- H, —OH,
- R is a member selected from the group of:
- —SO2Me, —SO2NH2, —CH2NH2, —CH2N(CF3)2;
- R1a is a member selected from the group of:
- H, —F;
- R1d1 and R1d2 is independently a member selected from the group of:
- H, —F, —Cl, —Br, —OMe; and
- R1e is a member selected from the group of:
- H, —OH,
and all pharmaceutically acceptable isomers, salts, hydrates, solvates and prodrug derivatives thereof.
- H, —OH,
and all pharmaceutically acceptable isomers, salts, hydrates, solvates and prodrug derivatives thereof.
and all pharmaceutically acceptable isomers, salts, hydrates, solvates and prodrug derivatives thereof.
- R1d3 is a member selected from the group consisting of:
- H, —F, —Cl, —Br, —OMe, —OCF3, —OCF2H, and —OCF2H;
and all pharmaceutically acceptable isomers, salts, hydrates, solvates and prodrug derivatives thereof.
and all pharmaceutically acceptable isomers, salts, hydrates, solvates and prodrug derivatives thereof.
and all pharmaceutically acceptable isomers, salts, hydrates, solvates and prodrug derivatives thereof.
- R1d3 is a member selected from the group consisting of:
- H, —F, —Cl, —Br, —OMe, —OCF3, —OCF2H, and —OCF2H,
and all pharmaceutically acceptable isomers, salts, hydrates, solvates and prodrug derivatives thereof.
wherein each of Ra, Rb, Rc, Rd and Re is independently a member selected from the group consisting of C1-C8 alkyl, C2-C8 alkenyl, C1-C8 acyl and C1-C8 acyl C1-C8 alkyl ester, and the Ra and Rb groups together with the nitrogen atom to which they are both attached may be cyclized to form a C3-C8 heterocylic ring having from 1 to 4 additional hetero ring atoms selected from O, N and S,
and all pharmaceutically acceptable isomers, salts, hydrates, solvates and prodrug derivatives thereof.
Claims (10)
A-Q-D-E-G-J-X (Ic)
Priority Applications (7)
Application Number | Priority Date | Filing Date | Title |
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US11/924,480 US7727981B2 (en) | 2000-02-29 | 2007-10-25 | Benzamides and related inhibitors of factor Xa |
US12/756,037 US8063036B2 (en) | 2000-02-29 | 2010-04-07 | Benzamides and related inhibitors of factor Xa |
US13/247,937 US8518977B2 (en) | 2000-02-29 | 2011-09-28 | Benzamides and related inhibitors of factor XA |
US13/612,597 US8691847B2 (en) | 2000-02-29 | 2012-09-12 | Benzamides and related inhibitors of factor Xa |
US14/175,087 US9108922B2 (en) | 2000-02-29 | 2014-02-07 | Benzamides and related inhibitors of factor Xa |
US14/742,465 US9629831B2 (en) | 2000-02-29 | 2015-06-17 | Benzamides and related inhibitors of factor XA |
US15/466,530 US10179124B2 (en) | 2000-02-29 | 2017-03-22 | Benzamides and related inhibitors of factor Xa |
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Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US18574600P | 2000-02-29 | 2000-02-29 | |
US09/663,420 US6844367B1 (en) | 1999-09-17 | 2000-09-15 | Benzamides and related inhibitors of factor Xa |
US09/794,225 US6376515B2 (en) | 2000-02-29 | 2001-02-28 | Benzamides and related inhibitors of factor Xa |
US10/126,976 US20030162690A1 (en) | 2000-02-29 | 2002-04-22 | Benzamides and related inhibitors of factor Xa |
US10/687,334 US6835739B2 (en) | 2000-02-29 | 2003-10-15 | Benzamides and related inhibitors of factor Xa |
US10/942,733 US7314874B2 (en) | 2000-02-29 | 2004-09-15 | Benzamides and related inhibitors of factor Xa |
US11/442,060 US7342013B2 (en) | 2000-02-29 | 2006-05-26 | Benzamides and related inhibitors of factor Xa |
US11/924,480 US7727981B2 (en) | 2000-02-29 | 2007-10-25 | Benzamides and related inhibitors of factor Xa |
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US11/442,060 Continuation US7342013B2 (en) | 2000-02-29 | 2006-05-26 | Benzamides and related inhibitors of factor Xa |
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US12/756,037 Continuation US8063036B2 (en) | 2000-02-29 | 2010-04-07 | Benzamides and related inhibitors of factor Xa |
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US09/794,225 Expired - Lifetime US6376515B2 (en) | 2000-02-29 | 2001-02-28 | Benzamides and related inhibitors of factor Xa |
US10/126,976 Abandoned US20030162690A1 (en) | 2000-02-29 | 2002-04-22 | Benzamides and related inhibitors of factor Xa |
US10/687,334 Expired - Lifetime US6835739B2 (en) | 2000-02-29 | 2003-10-15 | Benzamides and related inhibitors of factor Xa |
US10/942,733 Expired - Fee Related US7314874B2 (en) | 2000-02-29 | 2004-09-15 | Benzamides and related inhibitors of factor Xa |
US11/442,060 Expired - Lifetime US7342013B2 (en) | 2000-02-29 | 2006-05-26 | Benzamides and related inhibitors of factor Xa |
US11/488,455 Expired - Fee Related US7727982B2 (en) | 2000-02-29 | 2006-07-17 | Benzamides and related inhibitors of factor Xa |
US11/924,480 Expired - Fee Related US7727981B2 (en) | 2000-02-29 | 2007-10-25 | Benzamides and related inhibitors of factor Xa |
US12/756,037 Expired - Fee Related US8063036B2 (en) | 2000-02-29 | 2010-04-07 | Benzamides and related inhibitors of factor Xa |
US13/247,937 Expired - Fee Related US8518977B2 (en) | 2000-02-29 | 2011-09-28 | Benzamides and related inhibitors of factor XA |
US13/612,597 Expired - Fee Related US8691847B2 (en) | 2000-02-29 | 2012-09-12 | Benzamides and related inhibitors of factor Xa |
US14/175,087 Expired - Fee Related US9108922B2 (en) | 2000-02-29 | 2014-02-07 | Benzamides and related inhibitors of factor Xa |
US14/742,465 Expired - Fee Related US9629831B2 (en) | 2000-02-29 | 2015-06-17 | Benzamides and related inhibitors of factor XA |
US15/466,530 Expired - Fee Related US10179124B2 (en) | 2000-02-29 | 2017-03-22 | Benzamides and related inhibitors of factor Xa |
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